Substituted pyrazolopyrimidines and thiazolopyrimidines

ABSTRACT

Substituted pyrazolopyrimidines and thiazolopyrimidines are provided along with methods for production, treatment of medical conditions and illnesses, and formulations for use as pharmaceutical compositions.

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application is a continuation of International PatentApplication No. PCT/EP02/02722, filed Mar. 13, 2002, designating theUnited States of America, and published in German as WO 02/072585, theentire disclosure of which is incorporated herein by reference. Priorityis claimed based on Federal Republic of Germany patent application no.DE 101 12 197.0, filed Mar. 14, 2001, and based on Federal Republic ofGermany patent application no. DE 101 53 344.6, filed Oct. 29, 2001.

FIELD OF THE INVENTION

[0002] The present invention relates to substituted pyrazolopyrimidinesand thiazolopyrimidines, processes for their preparation, substancelibraries containing them, medicaments that contain these compounds, theuse of these compounds for the production of medicaments for thetreatment and/or prophylaxis of pain, epilepsy, schizophrenia,neurodegenerative conditions, in particular Alzheimer's disease,Huntington's disease and Parkinson's disease, cerebral ischaemias andinfarcts, psychoses due to raised amino acid levels, cerebral oedemas,insufficiency states of the central nervous system, in particular withhypoxias, especially neonatal hypoxia, and anoxias, AIDS dementia,encephalomyelitis, Tourette's syndrome, perinatal asphyxia, tinnitus,neuropathic pain, respiratory pathway diseases, cancer, cardiacarrhythmias, malfunctions and diseases of the immune system,inflammatory conditions and diseases, neurodegenerative conditions,Parkinson's disease, kidney failure, schizophrenia, sleep disturbances,strokes, thromboses, urinary incontinence, diabetes, psoriasis, septicshock, cerebral traumas, glaucoma and/or congestive insufficiency, aswell as pharmaceutical preparations containing these compounds.

BACKGROUND OF THE INVENTION

[0003] The treatment of chronic and non-chronic pain conditions is veryimportant in medicine. There is therefore a universal need for highlyeffective therapies for a patient-friendly and targeted treatment ofchronic and non-chronic pain conditions, including the successful andsatisfactory treatment of pain on the part of the patient.

[0004] Conventional opioids such as morphine are highly effective intreating severe to extremely severe pain. Their use is however limitedby the known side effects such as for example respiratory depression,vomiting, sedation, constipation and development of tolerance. Also,they are less effective in treating neuropathic or incidental painafflicting in particular tumour patients.

[0005] Opioids exert their analgesic effect by binding to cell membranereceptors that belong to the family of the so-called G protein-coupledreceptors. In addition to these there are further receptors as well asion channels that are significantly involved in the system of paingeneration and pain transmission, for example the N-methyl-D-aspartateion channel (NMDA ion channel), via which a substantial part of synapticcommunication proceeds and through which the calcium ion exchangebetween a neuronal cell and its environment is controlled (see forexample P. D. Leeson, L. L. Iversen, J. Med. Chem. 37 (1994) 4053-4067).

[0006] Important knowledge concerning the physiological importance ofion channel selective substances has been made possible by thedevelopment of the patch-clamp technique, by means of which the effectof NMDA antagonists (i.e. antagonists of the NMDA ion channel) on thecalcium level in the cell interior can be detected.

[0007] In the unactivated state the NMDA ion channels are in each caseclosed by individual magnesium ions that are present in the interior ofthe channel and cannot pass through the latter on account of their size.In the activated state the smaller calcium and sodium ions can passthrough the channel. The (+)-MK801 binding site of the NMDA ion channel(ionotropic NMDA receptor) is also present in the interior of thismembrane protein. Substances with an NMDA antagonistic action, such asphencyclidine (PCP), ketamine or MK801, occupy this binding site(so-called “channel blockers”) and accordingly close the relevant NMDAion channel.

SUMMARY OF THE INVENTION

[0008] One object of the present invention is to provide analgesicallyactive compounds that are suitable for relieving pain and possibly alsofor relieving chronic and neuropathic pain. In addition these substancesshould as far as possible produce none of the side effects that normallyoccur when using opioids such as morphine, for example nausea, vomiting,dependence, respiratory depression or constipation.

[0009] This object is achieved by the compounds of the general structure(I A), (I B) and (II), which are analgesically active and bind to theMK801 binding site of the NMDA receptor. The compounds according to theinvention are substituted pyrazolopyrimidines and thiazolopyrimidines ofthe general structure (I A), (I B) or (II)

[0010] wherein

[0011] R¹ and R² independently of one another denote H, O—R⁹, S—R¹⁰,C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl,—(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆ alkyl)-heterocyclyl,

[0012]  in which one of the radicals R¹ and R² is H and the otherradical of R¹ and R² is not H, or in the case that one of the radicalsR¹ and R² denotes aryl, the other radical of R¹ and R² denotes H orC₁₋₁₂-alkyl,

[0013] R³ and R⁴ denote H, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl in which at least oneof the radicals R³ and R⁴ is H, or

[0014] one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ forms W, where W denotes α′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6,α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′, α′-CH═CH—CH₂—CH₂-β′,α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′,

[0015]  α′-O—(CH₂)_(m)β′ where m=2, 3, 4 or 5,

[0016]  the end of W identified by α′ is joined to the atom of thecompound of the general structure (I A), (I B) or (II) identified by α,and the end of W identified by β′ is joined to the atom of the compoundof the general structure (I A), (I B) or (II) identified by p, the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, and the other radical of R³and R⁴ is H or C₁₋₁₂-alkyl;

[0017] R⁵ denotes C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl orC(═O)R¹¹;

[0018] R⁶ denotes H, C₁₋₈-alkyl, —CN, fluorine, chlorine, bromine,iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶ where p=0, 1 or 2,—C(═O)R¹⁷ or —N═N-aryl;

[0019] R⁷ denotes H, C₁₋₈-alkyl, aryl, —CN, fluorine, chlorine, bromine,iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2 ordenotes C(═O)R²⁰;

[0020] R⁸ denotes H, C₁₋₈-alkyl or aryl, or

[0021] the radicals R⁷ and R⁸ together form Y, where Y denotesβ′-CR²¹═CR²²—CR²³═CR²⁴-δ′ and the end of Y identified by γ is joined tothe atom of the general structure (II) identified by γ, and the end of Yidentified by δ′ is joined to the atom of the general structure (II)identified by δ;

[0022] R⁹ and R¹⁰ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0023] R¹¹ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl or OR²⁵;

[0024] R¹² denotes C₁₋₆-alkyl or —CH₂-aryl;

[0025] R¹³ and R¹⁴ are identical or different C₁₋₆-alkyl or togetherdenote —(CH₂)_(h)— where h=4 or 5;

[0026] R¹⁵ and R¹⁶ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0027] R¹⁷ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ or OR²⁶;

[0028] R¹⁸ and R¹⁹ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0029] R²⁰ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl or —(C₁₋₆-alkyl)-aryl or OR²⁷;

[0030] R²¹, R²², R²³ and R²⁴ independently of one another denote H,fluorine, chlorine, bromine, iodine or OR²⁸;

[0031] R²⁵, R²⁶, R²⁷ and R²⁸ independently of one another denote H orC₁₋₆-alkyl, where R²⁵ does not denote H if simultaneously R¹ denotesaryl and R² denotes alkyl.

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0032] The compounds according to the invention of the general structure(I A), (I B) or (II) in the represented form or in the form of theiracid(s) or their base(s) or in the form of one of their salts, inparticular one of their physiologically compatible salts, or in the formof one of their solvates, in particular the hydrates; in the form oftheir racemate, in the form of the pure stereoisomers, in particularenantiomers or diastereomers, or in the form of mixtures of thestereoisomers, in particular of the enantiomers or diastereomers, arepresent in an arbitrary mixture ratio. The compounds according to theinvention, in particular the pyrazolopyrimidines (I) according to theinvention, may be present in tautomeric forms, in the case of (I) in theforms (I A) and (I B), wherein the optionally preferred tautomeric formmay vary from compound to compound and for example depending on theaggregate state or on the chosen solvent.

[0033] The following compounds of the general structure (I A), (I B) or(II) are already known in the prior art, though their use has not beendescribed in a medicament or for the production of a medicament for thetreatment and/or prophylaxis of pain, epilepsy, schizophrenia,neurodegenerative conditions, in particular Alzheimer's disease,Huntington's disease and Parkinson's disease, cerebral ischaemias andinfarcts, psychoses due to raised amino acid levels, cerebral oedemas,insufficiency states of the central nervous system, in particular inhypoxias and anoxias, AIDS dementia, encephalomyelitis, Tourette'ssyndrome, perinatal asphyxia and tinnitus:4,5,6,7-tetrahydro-2-methyl-5,7-diphenylpyrazolo[1,5-a]pyrimidine,4,5,6,7-tetrahydro-2,5-dimethyl-7-phenyl-pyrazolo[1,5-a]pyrimidine,4,5,6,7-tetrahydro-5,7-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine,4,5,6,7-tetrahydro-2,5,7-trimethylpyrazolo[1,5-a]pyrimidine,4,5,6,7-tetrahydro-5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine (B.Koren et al., Tetrahedron (1976) 32, 493-497;4,5,6,7-tetrahydro-2-methyl-5,7-di-n-propylpyrazolo[1,5-a]pyrimidine-3-carbonitrile,4,5,6,7-tetrahydro-5-methyl-7-[3-(trifluoromethyl)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile,7-[4-chloro)-phenyl]-4,5,6,7-tetrahydro-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile,7-[3-chloro)-phenyl]-4,5,6,7-tetrahydro-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile(EP 0 264 773 A1);3,4-dihydro-2-(4-nitrophenyl)-4-phenyl-2H-pyrimido[2,1-b]benzothiazole,3,4-dihydro-4-(4-methylphenyl)-2-(4-nitrophenyl)-2H-pyrimido[2,1-b]benzothiazole(M. A. Abdel-Rahman et al., CA (1995) 796768 [Rev. Roum. Chim. (1995)42, 165-172]).

[0034] These compounds are therefore also the subject of the presentinvention, as are processes according to the invention for theirpreparation, substance libraries or medicaments containing them, as wellas their use for the production of medicaments for the treatment and/orprophylaxis of pain, epilepsy, schizophrenia, neurodegenerativeconditions, in particular Alzheimer's disease, Huntington's disease andParkinson's disease, cerebral ischaemias and infarcts, psychoses due toraised amino acid levels, cerebral oedemas, insufficiency states of thecentral nervous system, especially in hypoxias and anoxias, AIDSdementia, encephalomyelitis, Tourette's syndrome, perinatal asphyxia andtinnitus, as well as further medical conditions mentioned in thisdisclosure.

[0035] The terms “alkyl”, “C₁₋₁₂-alkyl”, “C₁₋₈-alkyl” and “C₁₋₆-alkyl”include within the scope of the present invention acyclic saturated orunsaturated hydrocarbon radicals that may be branched or straight-chainas well as unsubstituted or singly substituted or multiply identicallyor differently substituted with (as in the case of C₁₋₁₂-alkyl) 1 to 12(i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), with (as in the case ofC₁₋₁₂-alkyl) 1 to 8 (i.e. 1, 2, 3, 4, 5, 6, 7 or 8) or with (as in thecase of C₁₋₆-alkyl) 1 to 6 (i.e. 1, 2, 3, 4, 5 or 6) C atoms, i.e.C₁₋₁₂-alkanyls, C₁₋₈-alkanyls or C₁₋₆-alkanyls, C₂₋₁₂-alkenyls,C₂₋₈-alkenyls or C₂₋₆-alkenyls, and C₂₋₁₂-alkinyls, C₂₋₈-alkinyls orC₂₋₆-alkinyls. In this connection “alkinyls” have at least one C—Cdouble bond, and “alkinyls” have at least one C—C triple bond.Preferably alkyl is selected from the group comprising methyl, ethyl,n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-pentyl, isopentyl, neopentyl, n-hexyl, 2-hexyl, n-heptyl, n-octyl,n-nonyl, n-decyl, n-dodecyl; ethenyl (vinyl), ethinyl, propenyl(—CH₂CH═CH₂, —CH═CH—CH₃, —C(═CH₂)—CH₃), propinyl (—CH₂—C≡CH, —C≡C—CH₃),butenyl, butinyl, pentenyl, pentinyl, hexenyl, hexinyl, octenyl andoctinyl. “C₃₋₈-cycloalkyl” (or “cycloalkyl”) denotes within the contextof the present invention a cyclic saturated or unsaturated hydrocarbonradical with 3, 4, 5, 6, 7 or 8 C atoms, in which the radical may beunsubstituted or singly substituted or multiply identically ordifferently substituted and may optionally be benzo-condensed.Cycloalkyl denotes for example cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl,cycloheptenyl and cyclooctenyl. For the purposes of the presentinvention the following are particularly preferred: cyclopropyl,cyclopropyl-2-carboxylic acid, cyclopropyl-2-carboxylic acid ethyl esterand cyclohexyl.

[0036] For the purposes of the present invention the expression “aryl”is understood to denote a radical that is selected from the groupcomprising phenyl, naphthyl, anthracenyl and biphenyl, and isunsubstituted or is singly or multiply identically or differentlysubstituted. The aryl radicals may also be condensed with furthersaturated, (partially) unsaturated or aromatic ring systems. Each arylradical may be present unsubstituted or singly or multiply substituted,in which the aryl substituents may be identical or different and may bein any arbitrary position of the aryl radical. Advantageously aryldenotes aryl′, which includes aryl¹, aryl² and aryl³. In this connectionaryl¹ denotes

[0037] aryl² denotes

[0038] and aryl³ denotes

[0039] wherein R²⁹, R³⁰ and R³¹ independently of one another denote H,—C₁₋₆-alkyl, C₃₋₈-cycloalkyl, —(C₁₋₆ alkyl)-C₃₋₈-cycloalkyl, aryl, (C₁₋₆alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl, F, Cl, Br, I,—CN, —NC, —OR³², —SR³³, —NO, —NO₂, NH₂, NHR³⁴, NR³⁵R³⁶, —N—OH,—N—OC₁₋₆-alkyl, —NHNH₂, —N═N-aryl, —(C═O)R³⁷,

[0040] where d=1, 2 or 3, or denote —(C═S)R³⁷, and may be in anyarbitrary ring position;

[0041] R³² and R³³ independently of one another denote H, —C₁₋₆-alkyl,—C₃₋₈-cycloalkyl, —(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl,—(C₁₋₆-alkyl)-aryl, -heterocyclyl, —(C₁₋₆-alkyl)-heterocyclyl, (C═O)R³⁸,—[(CH₂)_(w)—O]_(z)—H or —[(CH₂)_(w)—O]_(z)—C₁₋₆-alkyl where w=1, 2, 3 or4 and z=1, 2, 3, 4 or 5;

[0042] R³⁴ denotes C₁₋₆-alkyl, —CH₂-aryl or —(C═O)O-tert.-butyl;

[0043] R³⁵ and R³⁶ independently of one another denote C₁₋₆-alkyl ortogether denote —(CH₂)—_(g) where g=4 or 5;

[0044] R³⁷ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)—C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl, -heterocyclyl,—(C₁₋₆-alkyl)-heterocyclyl, —OR³⁹, —NH₂, —NHR³⁴, —NR³⁵R³⁶;

[0045] R³⁸ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)—C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl; and

[0046] R³⁹ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)—C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl, -heterocyclylor —(C₁₋₆-alkyl)-heterocyclyl.

[0047] Particularly preferred aryl radicals for the purposes of theinvention are phenyl, 3-fluorophenyl, 3-bromophenyl, 4-bromophenyl,4-chlorophenyl, 4-fluorophenyl, 3-methylphenyl, 4-methylphenyl,4-hydroxyphenyl, 4-methoxyphenyl, 2,4-dimethylphenyl,3,4-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 2-naphthyl,4-trifluorophenyl, 4-phenoxyphenyl, 2-hydroxy-3-methoxyphenyl,4-hydroxy-3-methoxyphenyl and 3-carboxy-2-hydroxyphenyl.

[0048] The expression “heterocyclyl” denotes a monocyclic or polycyclicorganic radical in which at least one ring contains 1 heteroatom or 2,3, 4 or 5 identical or different heteroatoms that is/are selected fromthe group comprising N, O and S, wherein the radical is saturated orunsaturated, and is unsubstituted or singly substituted or multiplyidentically or differently substituted. Examples of heterocyclylradicals within the scope of the present invention are monocyclic5-membered, 6-membered or 7-membered organic radicals containing 1heteroatom or 2, 3, 4 or 5 identical or different heteroatoms thatis/are nitrogen, oxygen and/or sulfur, and their benzo-condensedanalogues. The “heteroaryl” radicals form a subgroup of the heterocyclylradicals, and comprise those heterocyclyl radicals in which the at leastone ring that contains the heteroatom(s) is heteroaromatic. Eachheteroaryl radical may be present unsubstituted or singly substituted ormultiply identically or differently substituted. Examples ofheterocyclyl radicals within the context of the present invention arepyrrolidinyl, tetrahydrofuryl, piperidinyl, piperazinyl and inparticular morpholinyl. Examples of heterocyclyl radicals that are atthe same time heteroaryl radicals are pyrrolyl, pyrazolyl, imidazolyl,pyridazinyl, pyrimidinyl, pyrazinyl and in particular furanyl, thienyland pyridinyl as well as their benzo-condensed analogues. All theseradicals may in each case be present unsubstituted or singly ormultiply, identically or differently substituted.

[0049] The expressions “(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl”,“(C₁₋₆-alkyl)-heterocyclyl” and “(C₁₋₆-alkyl)-aryl” denote, for thepurposes of the present invention, that the cycloalkyl, heterocyclyl oraryl radical is bound via a C₁₋₆-alkyl group to the compound with whichit is substituted. The same comments apply to the expression“CH₂—C₃₋₈-cycloalkyl”.

[0050] In connection with the expressions “alkyl”, “alkanyl”, “alkenyl”,“alkinyl” and “cycloalkyl”, the term “substituted” within the meaning ofthe present invention is understood to mean the replacement of ahydrogen atom by for example F, Cl, Br, I, —CN, —NC, NH₂, NH-alkyl,NH-aryl, NH-alkyl-aryl, NH-heterocyclyl, NH-alkyl-OH, N(alkyl)₂,N(alkyl-aryl)₂, N(heterocyclyl)₂, N(alkyl-OH)₂, NO, NO₂, SH, S-alkyl,S-aryl, S-alkyl-aryl, S-heterocyclyl, S-alkyl-OH, S-alkyl-SH, OH,O-alkyl, O-aryl, O-alkyl-aryl, O-heterocyclyl, O-alkyl-OH, CHO,C(═O)C₁₋₆-alkyl, C(═S)C₁₋₆-alkyl, C(═O)aryl, C(═S)aryl,C(═O)C₁₋₆-alkyl-aryl, C(═S)C₁₋₆-alkyl-aryl, C(═O)-heterocyclyl,C(═S)-heterocyclyl, CO₂H, CO₂-alkyl, CO₂-alkyl-aryl, C(═O)NH₂,C(═O)NH-alkyl, C(═O)NH-aryl, C(═O)NH-heterocyclyl, C(═O)N(alkyl)₂,C(═O)N(alkyl-aryl)₂, C(═O)N(heterocyclyl)₂, SO-alkyl, SO₂-alkyl,SO₂-alkyl-aryl, SO₂NH₂, SO₃H, SO₃-alkyl, cycloalkyl, aryl orheterocyclyl, in which multiply substituted radicals are understood tomean those radicals that are multiply substituted, e.g. doubly or triplysubstituted, either on different atoms or on the same atom, for exampletriply substituted on the same C atom as in the case of CF₃ or —CH₂CF₃,or at different positions, as in the case of —CH(OH)—CH═CCl—CH₂Cl. Themultiple substitution may be carried out with the same or with differentsubstituents. Particularly preferred for the purposes of the presentinvention are CF₃ and CH₂—CH₂—OH as substituted alkyl as well ascyclopropyl-2-carboxylic acid and cyclopropyl-2-carboxylic acid ethylester as substituted cycloalkyl.

[0051] With reference to “aryl”, “heterocyclyl” as well as “heteroaryl”,within the context of the present invention the term “singlysubstituted” or “multiply substituted” is understood to denote thesingle or multiple substitution, e.g. double, triple or fourfoldsubstitution, of one or more hydrogen atoms of the ring system by asuitable substituent. Insofar as the meaning of this suitablesubstituent in connection with “aryl”, “heterocyclyl” or “heteroaryl” isnot defined in another place in the description or in the claims,suitable substituents are F, Cl, Br, I, —CN, —NC, NH₂, NH-alkyl,NH-aryl, NH-alkyl-aryl, NH-heterocyclyl, NH-alkyl-OH, N(alkyl)₂,N(alkyl-aryl)₂, N(heterocyclyl)₂, N(alkyl-OH)₂, NO, NO₂, SH, S-alkyl,S-cycloalkyl, S-aryl, S-alkyl-aryl, S-heterocyclyl, S-alkyl-OH,S-alkyl-SH, OH, O-alkyl, O-cycloalkyl, O-aryl, O-alkyl-aryl,O-heterocyclyl, O-alkyl-OH, CHO, C(═O)C₁₋₆-alkyl, C(═S)C₁₋₆-alkyl,C(═O)aryl, C(═S)aryl, C(═O)C₁₋₆-alkyl-aryl, C(═S)C₁₋₆-alkyl-aryl,C(═O)-heterocyclyl, C(═S)-heterocyclyl, CO₂H, CO₂-alkyl, CO₂-alkyl-aryl,C(═O)NH₂, C(═O)NH-alkyl, C(═O)NH-aryl, C(═O)NH-heterocyclyl,C(═O)N(alkyl)₂, C(═O)N(alkyl-aryl)₂, C(═O)N(heterocyclyl)₂, S(O)-alkyl,S(O)-aryl, SO₂-alkyl, SO₂-aryl, SO₂NH₂, SO₃H, CF₃, ═O, ═S, alkyl,cycloalkyl, aryl and/or heterocyclyl; on one or optionally various atoms(in which connection a substituent may optionally in turn besubstituted). The multiple substitution is performed with the same orwith different substituents.

[0052] “Benzo-condensed” denotes for the purposes of the presentinvention that a benzene ring is condensed onto another ring.

[0053] Pharmaceutically acceptable or physiologically compatible saltswithin the context of the present invention are those salts of thecompounds according to the invention according to the general structure(I A), (I B) and/or (II) that when used for pharmaceutical purposes,especially in mammals and/or humans, are physiologically compatible.Such pharmaceutically acceptable salts may be formed for example withinorganic or organic acids, or in the case where the compounds accordingto the invention are carboxylic acids, may be formed with bases.

[0054] Preferably the pharmaceutically acceptable salts of the compoundsaccording to the invention according to the general structure (I A), (IB) or (II) are formed with hydrochloric acid, hydrobromic acid, sulfuricacid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid,carbonic acid, formic acid, acetic acid, oxalic acid, succinic acid,tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid,glutamic acid or aspartic acid. If the compounds according to theinvention are carboxylic acids, the pharmaceutically acceptable saltsmay also be formed by reaction with bases, such as for example sodiumhydrogen carbonate or sodium carbonate. The salts that are formedinclude, inter alia, hydrochlorides, hydrobromides, phosphates,carbonates, hydrogen carbonates, formates, acetates, oxalates,succinates, tartrates, fumarates, citrates and glutamates or sodiumsalts. Particularly preferred are the hydrochlorides. Also preferred arethe hydrates of the compounds according to the invention, which may beobtained for example by crystallisation from aqueous solution.

[0055] All compounds according to the invention contain at least oneasymmetry centre, namely the carbon atom of the structure (I A), (I B)or (II) substituted by R⁵.

[0056] Accordingly the compounds according to the invention according tothe general structure (I A), (I B) or (II) may be present in the form oftheir racemates, in the form of the pure enantiomers and/ordiastereomers or in the form of mixtures of these enantiomers and/ordiastereomers, and more specifically both as the substance per se aswell as pharmaceutically acceptable salts of these compounds. Themixtures may be present in any arbitrary mixture ratio of thestereoisomers. Preferably the compounds of the general structure (I A),(I B) or (II) are present as enantiomer-pure compounds.

[0057] Preferred are those compounds of the general formulae (I A), (IB) or (II) or their pharmaceutically acceptable salts in which

[0058] R¹ and R² independently of one another denote H, O—R⁹, S—R¹⁰,C₁₋₆-alkyl, aryl′ or —(C₁₋₆-alkyl)-aryl′, wherein the aryl′ substituentsR²⁹, R³⁰ and R³¹ independently of one another denote H, C₁₋₆-alkyl, F,Cl, Br, I, OH, O—C₁₋₆-alkyl, O-aryl¹ or O—CH₂-aryl¹,

[0059]  wherein one of the radicals R¹ and R² is H and the other radicalof R¹ and R² is not H, or in the case that one of the radicals R¹ and R²denotes aryl′, the other radical of R¹ and R² denotes H or C₁₋₆-alkyl,

[0060] R³ and R⁴ denote H, unsubstituted or singly substituted ormultiply identically or differently substituted methyl, ethyl, n-propyl,2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl,sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, aryl′ or —CH₂-aryl′, whereinat least one of the radicals R³ and R⁴ is H, or

[0061] one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ forms W, where W denotes α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′,α′-O— (CH₂)_(m)-β′ where m=2, 3, 4 or 5,

[0062]  the end of W identified by α′ is joined to the atom of thecompound of the general structure (I A), (I B) or (II) identified by α,and the end of W identified by β′ is joined to the atom of the generalstructure (I A), (I B) or (II) identified by β, the other radical of R¹and R² is H or methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl,sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexylor sec.-hexyl and the other radical of R³ and R⁴ denotes H or methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl;

[0063] R⁵ denotes methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl,sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl,sec.-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl orcycloheptyl that in each case is unsubstituted or singly substituted ormultiply identically or differently substituted, or denotes aryl′ or—(CH₂)_(k)-aryl′, where k=1,2,3 or 4, heterocyclyl or C(═O)R¹¹;

[0064] R⁶ denotes H, methyl, ethyl, —CN, fluorine, chlorine, bromine,iodine, —C(═O)R¹⁷ or —N═N-aryl¹;

[0065] R⁷ denotes H, aryl¹, OR¹⁸, S(O)_(q)R¹⁹, where q=0, 1 or 2, ordenotes unsubstituted or singly substituted or multiply identically ordifferently substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl,isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl,isohexyl or sec.-hexyl,

[0066] R⁸ denotes H or aryl′, or

[0067] the radicals R⁷ and R⁸ together form Y, where Y denotesγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′ and the end of Y identified by γ′ is joined tothe atom of the general structure (II) identified by γ, and the end of Yidentified by δ′ is joined to the atom of the general structure (II)identified by δ;

[0068] R⁹ denotes unsubstituted or singly substituted or multiplyidentically or differently substituted methyl, ethyl, n-propyl,2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl,sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl or cycloheptyl or denotes —[(CH₂)_(r)—O]_(s)—Hwhere r=1, 2, 3, 4, 5 or 6 and s=1, 2, 3, 4, 5 or 6;

[0069] R¹⁰ denotes aryl′;

[0070] R¹¹ denotes aryl′ or OR²⁵;

[0071] R¹⁷ denotes OR²⁶;

[0072] R¹⁸ denotes H or methyl;

[0073] R¹⁹ denotes H, aryl¹, or in each case unsubstituted, singlysubstituted or multiply identically or differently substituted methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl;

[0074] R²¹, R²², R²³ and R²⁴ independently of one another denote H,fluorine, chlorine, bromine, iodine or OR²⁸;

[0075] R²⁵ denotes H, methyl, ethyl, n-propyl, 2-propyl, n-butyl,isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl,isohexyl or sec.-hexyl, where R²⁵ does not denote H if at the same timeR¹ denotes aryl and R² denotes alkyl; R²⁶ denotes H, methyl, ethyl,n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl,isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl; and

[0076] R²⁸ denotes H, methyl or ethyl;

[0077] Heterocyclyl denotes furan-2-yl, furan-3-yl, thien-2-yl,thien-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, where furanyl,thienyl and pyridinyl are in each case unsubstituted or singlysubstituted or multiply identically or differently substituted;

[0078] Aryl′ denotes aryl¹, aryl² or aryl³;

[0079] Aryl¹ denotes

[0080] Aryl² denotes

[0081] Aryl³ denotes

[0082] R²⁹, R³⁰ and R³ independently of one another denote H,C₁₋₆-alkyl, C₃₋₈-cycloalkyl, (C₁₋₆ alkyl)-C₃₋₈-cycloalkyl, aryl,(C₁₋₆-alkyl)-aryl, heterocyclyl, (C₁₋₆ alkyl)-heterocyclyl, F, Cl, Br,I, —CN, —NC, —OR³², —SR³³, —NO, —NO₂, NH₂, NHR³⁴, NR³⁵R³⁶, —N—OH,—N—OC₁₋₆-alkyl, —NHNH₂, —N═N-aryl, —(C═O)R³⁷,

[0083]  where d=1, 2 or 3, or denotes —(C═S)R³⁷, and may be in anyarbitrary ring position;

[0084] R³² and R³³ independently of one another denote H, —C₁₋₆-alkyl,—C₃₋₈-cycloalkyl, —(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl,—(C₁₋₆-alkyl)-aryl, -heterocyclyl, —(C₁₋₆-alkyl)-heterocyclyl, (C═O)R³⁸,—[(CH₂)_(w)—O]_(z)—H or —[(CH₂)_(w)—O]_(z)—C₁₋₆-alkyl where w=1, 2, 3 or4 and z=1, 2, 3, 4 or 5;

[0085] R³⁴ denotes C₁₋₆-alkyl, —CH₂-aryl or —(C═O)O-tert.-butyl;

[0086] R³⁵ and R³⁶ independently of one another denote C₁₋₆-alkyl ortogether denote —(CH₂)—_(g) where g=4 or 5;

[0087] R³⁷ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl, -heterocyclyl,—(C₁₋₆-alkyl)-heterocyclyl, —OR³⁹, —NH₂, —NHR³⁴NR³⁵R³⁶;

[0088] R³⁸ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl; and

[0089] R³⁹ denotes H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl, -heterocyclylor —(C₁₋₆-alkyl)-heterocyclyl.

[0090] Among these compounds those are particularly preferred in which

[0091] R¹ and R² independently of one another denote H, O—R⁹, S—R¹⁰,unsubstituted or singly substituted or multiply identically ordifferently substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl,tert.-butyl or n-hexyl, aryl′ or —CH₂-aryl′, where the aryl′substituents R²⁹, R³⁰ and R³¹ independently of one another denote H,methyl, ethyl, 2-propyl, n-butyl, tert.-butyl, n-hexyl, F, Cl, Br, I,OH, O-methyl, O-ethyl,

[0092]  wherein one of the radicals R¹ and R² is H and the other radicalof R¹ and R² is not H, or in the case that one of the radicals R¹ and R²denotes aryl′, the other radical of R¹ and R² denotes H or methyl,ethyl, n-propyl, 2-propyl, n-butyl, tert.-butyl or n-hexyl,

[0093] R³ and R⁴ denote H, methyl or aryl¹, wherein the aryl¹substituents R²⁹, R³⁰ and R³¹ independently of one another are H, methylor O-methyl,

[0094]  wherein at least one of the radicals R³ and R⁴ is H, or

[0095] one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ forms W, where W denotes α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′,α′-O— (CH₂)_(m)-β′, where m=2, 3, 4 or 5

[0096]  the end of W identified by α′ is joined to the atom of thecompound of the general structure (I A), (I B) or (II) identified by α,and the end of W identified by β′ is joined to the atom of the compoundof the general structure (I A), (I B) or (II) identified by β, the otherradical of R¹ and R² and the other radical of R³ and R⁴ in each casedenotes H;

[0097] R⁵ denotes methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl,sec.-butyl, tert.-butyl, —(CH₂)₄—OH, cyclopropyl, where cyclopropyl isunsubstituted or singly substituted by C(═O)OH, C(═O)O-methyl orC(═O)O-ethyl, or denotes cyclopentyl, cyclohexyl, aryl¹ or—(CH₂)_(k)-aryl¹ where the aryl¹ substituents R²⁹, R³⁰ and R³¹independently of one another denote H, OH, —O-methyl, O—C₆H₅, CH₃, CF₃or C(═O)OH and k=1 or 2, or denotes heterocyclyl or C(═O)R¹¹;

[0098] R⁶ denotes H, —CN, bromine, —C(═O)R¹⁷ or —N═N-phenyl;

[0099] R⁷ denotes H, aryl¹ where R²⁹, R³⁰ and R³¹ are H, OH,S(O)_(q)R¹⁹, where q=0 or 2, or denotes methyl, ethyl, n-propyl,2-propyl, n-butyl, isobutyl, sec.-butyl or tert.-butyl,

[0100] R⁸ denotes H, aryl¹ where the aryl¹ substituents R²⁹, R³⁰ and R³¹independently of one another are H, methyl or chlorine, or denotes aryl³where R²⁹, R³⁰ and R³¹ are H, or

[0101] the radicals R⁷ and R⁸ together form Y, where Y denotesγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′ and the end of Y identified by γ′ is joined tothe atom of the general structure (II) identified by γ, and the end of Yidentified by δ′ is joined to the atom of the general structure (II)identified by δ;

[0102] R⁹ denotes methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl,sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl,sec.-hexyl, cyclopropyl, cyclopentyl or cyclohexyl or denotes—[(CH₂)_(r)—O]_(s)—H where r=1, 2 or 3 and s=1 or 2;

[0103] R¹⁰ denotes aryl¹;

[0104] R¹¹ denotes aryl¹ where R²⁹, R³⁰ and R³¹ denote H or OR²⁵;

[0105] R¹⁷ denotes OR²⁶;

[0106] R¹⁹ denotes methyl or aryl¹, where one of the aryl¹ substituentsR²⁹, R³⁰ and R³¹ is H or —NO₂, and the two other aryl¹ substituents ofR²⁹, R³⁰ and R³¹ are H;

[0107] R²¹ and R²³ denote H;

[0108] R²² denotes H, fluorine or OR²⁸;

[0109] R²⁴ denotes H or chlorine;

[0110] R²⁵ denotes H, methyl or ethyl, where R²⁵ does not denote H if atthe same time R¹ denotes aryl and R² denotes alkyl;

[0111] R²⁶ denotes H, methyl or ethyl;

[0112] R²⁸ denotes methyl or ethyl; and

[0113] Heterocyclyl denotes furan-2-yl, furan-3-yl, thien-2-yl,thien-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, where furanyl,thienyl and pyridinyl are in each case unsubstituted or singlysubstituted or multiply identically or differently substituted by —NO₂,—CH₃ or C(═O)OH.

[0114] Most particularly preferred compounds according to the inventionof the general structure (I A), (I B) or (II) are those in which

[0115] R¹ and R¹ independently of one another denote H, O—CH₂—CH₂—OH,O-cyclohexyl, S-phenyl, methyl, phenyl, 3-fluorophenyl, 3-bromophenyl,4-bromophenyl, 4-chlorophenyl, 4-fluorophenyl, 3-methylphenyl,4-hydroxyphenyl, 4-methoxyphenyl, 2,4-dimethylphenyl,3,4-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 2-naphthyl or —CH₂-phenyl,

[0116] R³ and R⁴ denote H, methyl or 4-methoxyphenyl, where at least oneof the radicals R³ and R⁴ is H, or

[0117] one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ form W, where W denotes α′-CH═CH—CH₂—β′, α′-CH═CH—CH₂—CH₂-β′,α′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5,

[0118]  the end of W identified by α′ is joined to the atom of thecompound of the general structure (I A), (I B) or (II) identified by α,and the end of W identified by β′ is joined to the atom of the compoundof the general structure (I A), (I B) or (II) identified by β, and theother radical of R¹ and R² and the other radical of R³ and R⁴ in eachcase denote H;

[0119] R⁵ denotes n-propyl, n-butyl, tert.-butyl, —(CH₂)₄—OH,cyclopropyl, cycloprop-2-yl-1-carboxylic acid ethyl ether, cyclohexyl,4-trifluorophenyl, 4-phenoxyphenyl, 2-hydroxy-3-methoxyphenyl,4-hydroxy-3-methoxyphenyl, 3-carboxy-2-hydroxy-phenyl, —(CH₂)₂-phenyl,5-carboxyfuran-2-yl, 5-methylfuran-2-yl, 5-nitrofuran-2-yl,5-nitro-thien-2-yl, pyridin-2-yl, pyridin-3-yl, C(═O)-phenyl, C(═O)OH orC(═O)Oethyl, where R⁵ does not denote C(═O)OH if at the same time R¹denotes aryl and R² denotes alkyl;

[0120] R⁶ denotes H, —CN, bromo, —C(═O)OH, —C(═O)Oethyl or —N═N-phenyl;

[0121] R⁷ denotes H, phenyl, OH, —S-methyl, —SO₂-(4-nitrophenyl) ortert.-butyl;

[0122] R⁸ denotes 4-chlorophenyl, 4-methylphenyl or 2-naphthyl; or

[0123] the radicals R⁷ and R⁸ together form Y, where Y denotesγ′-CR²¹═CH—CH═CH-δ′ and the end of Y identified by γ′ is joined to theatom of the general structure (II) identified by γ, and the end of Yidentified by δ′ is joined to the atom of the general structure (II)identified by δ; and

[0124] R²¹ denotes fluorine, methoxy or ethoxy.

[0125] Exemplary and advantageous compounds of the present invention areselected from the group that comprises

[0126]3-bromo-5-(5-nitrofuran-2-yl)-7-m-tolyltetrahydropyrazolo[1,5-a]pyrimidine

[0127]3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0128]3-bromo-7-naphthalin-2-yl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0129]2-(3-bromo-7-m-tolyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-cyclopropanecarboxylicacid ethyl ester

[0130]2-[3-bromo-7-(4-bromophenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester

[0131]2-(3-bromo-7-naphthalin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-cyclopropanecarboxylicacid ethyl ester

[0132]3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-methylfuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0133]3-bromo-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0134]3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0135]3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid

[0136]3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0137]3-bromo-7-(4-methoxyphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0138]5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic aciddiethyl ester;5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic aciddiethyl ester

[0139]2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester

[0140]2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester

[0141]3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester

[0142]7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid diethyl ester

[0143]3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0144]2-hydroxy-7-(4-hydroxyphenyl)-6-methyl-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0145]3-bromo-7-(4-hydroxyphenyl)-6-methyl-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0146]5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3,5-dicarboxylicacid diethyl ester;5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3,5-dicarboxylicacid diethyl ester

[0147]2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylicacid ethyl ester;2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylicacid ethyl ester

[0148]7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid diethyl ester

[0149]3-cyano-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0150]3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid

[0151]7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid-3-ethyl ester

[0152]3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0153]3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0154]7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3,5-dicarboxylicacid-3-ethyl ester

[0155]3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid

[0156]3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid

[0157]3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid

[0158]3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid

[0159]7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0160]7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0161]3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-2-phenylazotetrahydropyrazolo[1,5-a]pyrimidine

[0162]7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0163]7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0164]3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine

[0165]7-(4-methoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0166]7-(2,4-dimethylphenyl)-5-(2-ethoxycarbonylcyclopropyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0167]2-[7-(2,4-dimethylphenyl)-2-hydroxy-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester

[0168]2-[2-tert.-butyl-7-(2,4-dimethylphenyl)tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester

[0169]2-[3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester

[0170]2-[3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester

[0171]5-(2-ethoxycarbonylcyclopropyl)-7-(3-fluorophenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0172]2-[3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester

[0173]2-[7-(3-bromophenyl)-3-cyano-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester

[0174]7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0175]7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0176]7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0177]7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0178]7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0179]3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine

[0180]7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0181]7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0182]7-(4-methoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0183]5-[3-bromo-7-(4-methoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-furan-2-carboxylicacid

[0184]5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0185]5-benzoyl-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0186]5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile

[0187]5-benzoyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0188][3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone

[0189]5-benzoyl-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0190]5-benzoyl-7-(3,4-dimethoxyphenyl)tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0191]5-benzoyl-7-(4-methoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0192]5-benzoyl-7-(4-methoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0193]5-benzoyl-7-(4-methoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile

[0194]5-benzoyl-7-(3-fluorophenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0195][3-bromo-7-(3-fluorophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone

[0196][3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone

[0197]7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0198]3-bromo-7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine

[0199]7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0200]7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0201]7-(3,4-dimethoxyphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0202]7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0203]3-[3-cyano-7-(4-hydroxyphenyl)-6-methyltetrahydro-pyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid

[0204]3-(3-cyano-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoicacid;3-(3-cyano-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoicacid

[0205]3-(3-cyano-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid

[0206]3-[2-tert.-butyl-7-(4-chlorophenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid

[0207]5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0208]5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0209]5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carboxylicacid ethyl ester;5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta-[c]fluorene-3-carboxylicacid ethyl ester

[0210]4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol;4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol

[0211]5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile

[0212]5-(4-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0213]4-(2-tert.-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol

[0214]4-(3-bromo-2-phenyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol

[0215]5-(2-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0216]7-(4-chlorophenyl)-5-(2-hydroxy-3-methoxyphenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0217]5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile

[0218]5-(4-hydroxybutyl)-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0219]5-(4-hydroxybutyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0220]7-(4-chlorophenyl)-5-(4-hydroxybutyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0221]5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;

[0222]5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile

[0223]5-butyl-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0224]5-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0225]5-butyl-7-(4-chlorophenyl)-7-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0226]5-cyclopropyl-7-(2,4-dimethylphenyl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0227]2-tert.-butyl-5-cyclopropyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0228]5-cyclopropyl-7-(2,4-dimethylphenyl)-2-methylsulfanyltetrahydro-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0229]2-tert.-butyl-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0230]3-bromo-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine

[0231]5-cyclopropyl-7-(4-methoxyphenol)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0232]5-cyclopropyl-3,5,5a,6,7,11b-hexahydro-1,4,11c-triazacyclopenta[c]phenanthrene-3-carbonitrile

[0233]7-(2,4-dimethylphenyl)-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0234]7-(2,4-dimethylphenyl)-3-phenylazo-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0235]3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine

[0236]7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0237]7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0238]7-(3,4-dimethoxyphenyl)-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0239]5-cyclopropyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0240]2-(2-tert.-butyl-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-7-yloxy)-ethanol

[0241]5-cyclopropyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester;5-cyclopropyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester

[0242]5-cyclopropyl-3-phenylazo-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol;5-cyclopropyl-3-phenylazo-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol

[0243]7-cyclohexyloxy-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carboxylicacid ethyl ester

[0244]7-cyclohexyloxy-5-cyclopropyl-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-3-carbonitrile

[0245]7-(4-chlorophenyl)-5-cyclohexyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carbonitrile

[0246]5-cyclohexyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0247]5-cyclohexyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester;5-cyclohexyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester

[0248]5-cyclohexyl-7-cyclohexyloxytetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0249]7-(2,4-dimethylphenyl)-3-phenylazo-5-propyltetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0250]7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-propyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0251]5-tert.-butyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0252]2,5-di-tert.-butyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine

[0253]3-bromo-5-tert.-butyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine

[0254]2-[3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester

[0255]3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid

[0256]4-[3-bromo-6-methyl-2-phenyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl]-phenol

[0257]7-(4-hydroxyphenyl)-6-methyl-2-methylsulfanyl-5-(4-trifluoro-methylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0258]7-(4-hydroxyphenyl)-6-methyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0259]2-(4-nitrophenylsulfonyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine

[0260]3-(4-chlorophenyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine

[0261]5-phenylsulfanyl-7-pyridin-2-yl-3-p-tolyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine

[0262]7-methoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene

[0263]7-ethoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene

[0264]7-fluoro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene

[0265]3-naphthalin-2-yl-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine

[0266]7-phenyl-3-phenylazo-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0267]3-phenylazo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol

[0268]3-bromo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

[0269]7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0270]7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0271]3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine

[0272]3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0273]3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine

[0274]3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0275]3-cyano-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid ethyl ester

[0276]3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

[0277]7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

[0278]7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile

[0279]7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester

[0280] as well as their pharmaceutically acceptable salts.

[0281] The present invention also relates to processes for theproduction of the compounds of the structure (I A), (I B) and (II)according to the invention.

[0282] Accordingly, the compounds of the general structure (I A) and (IB) as well as their pharmaceutically acceptable salts

[0283] wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as defined above, canbe prepared by reacting a pyrazolamine of the general structure (IIIA)and/or (IIIB)

[0284] wherein R⁶ and R⁷ are as defined above, with an aldehyde of thegeneral structure (IV)

[0285] wherein R⁵ is as defined above, and with an olefin of the generalstructure (V)

[0286] wherein R¹, R², R³ and R⁴ are as defined above, with the provisothat if one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ forms W, the end of W identified by α′ is joined to theα-carbon atom of the olefin of the general structure (V), and the end ofW identified by β′ is joined to the β-carbon atom of the olefin of thegeneral structure (V), in the presence of an acid.

[0287] Accordingly the compounds of the general structure (II) accordingto the invention as well as their pharmaceutically acceptable salts

[0288] wherein R¹, R², R³, R⁴, R⁵, R⁷ and R⁸ are as defined above, canbe obtained by reacting a thiazolamine of the general structure (VI)

[0289] wherein R⁷ and R⁸ are as defined above, with the proviso that ifR⁷ and R⁸ form Y, the end of Y identified by γ′ is coupled to the atomof the thiazolamine of the general structure (VI) identified by γ andthe end of Y identified by δ′ is coupled to the atom of the thiazolamineof the general structure (VI) identified by δ, with an aldehyde of thegeneral structure (IV)

[0290] wherein R⁵ is as defined above, and with an olefin of the generalstructure (V)

[0291] wherein R¹, R², R³ and R⁴ are as defined above, with the provisothat if one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ form W, the end of W identified by α′ is joined to theα-carbon atom of the olefin of the general structure (V) and the end ofW identified by β′ is joined to the β-carbon atom of the olefin of thegeneral structure (V), in the presence of an acid.

[0292] The processes according to the invention are preferably carriedout in a “one-pot” reaction, in which a heterocyclylamine of the generalstructure (II A), (II B) or (VI), an aldehyde of the general structure(IV) and an olefin of the general structure (V) are simultaneouslyreacted with one another.

[0293] The acid that is used is an inorganic or organic protonic orLewis acid. Preferably the reaction is carried out in the presence of anorganic acid, for example acetic acid, trifluoroacetic acid ormethanesulfonic acid, especially trifluoroacetic acid.

[0294] The production process according to the invention may be carriedout in any suitable solvent in which the reactants are sufficientlysoluble. Preferably organic solvents are used, for exampledichloromethane or in particular acetonitrile.

[0295] The processes according to the invention are conveniently carriedout at a temperature of 0° to 100° C., in particular 15° to 40° C. Thereaction time is preferably 15 minutes to 12 hours and may be adapted tothe respective requirements.

[0296] All heterocyclylamines of the general structure (III) or (VI),the aldehydes of the general structure (IV) and the olefins of thegeneral structure (V) that are used in the processes according to theinvention are commercially available (from Acros, Geel; Avocado, Port ofHeysham; Aldrich, Delsenhofen; Fluka, Seelze; Lancaster, Mülheim;Maybridge, Tintagel; Merck, Darmstadt; Sigma, Deisenhofen; TCI, Japan)or may be prepared according to processes generally known in the priorart.

[0297] The processes according to the invention may also be carried outin semi-automated or fully automated form as parallel synthesis of agroup of compounds of the general structure (I A), (I B) and/or (II)according to the invention. Accordingly, substance libraries thatcontain at least one compound and preferably at least 48, in particular96 and most particularly preferably 384 compounds of the generalstructure (I A), (I B) or (II) as defined above are also the subject ofthe present invention.

[0298] For the purposes of the present invention the expression“substance library” is understood to denote a group of compounds thatare prepared according to the same process under identical or almostidentical reaction conditions and by varying one reactant or severalreactants. Such a substance library may contain the library items bothas individual pure compounds as well as in the form of a mixture ofthese compounds. With the aid of this substance library a medicalscreening for example may be performed in an automated manner in one orseveral in vitro screening processes.

[0299] The compounds of the general structure (I A) and/or (I B) or (II)may be isolated both as the substance per se as well as in the form of asalt. The substances of the general structure (I A), (I B) or (II) areusually obtained by reaction according to the process outlined abovefollowed by conventional working-up. The compounds that are therebyobtained may then be converted into the corresponding salt by forexample adding an inorganic or organic acid, preferably hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonicacid, p-toluenesulfonic acid, carbonic acid, formic acid, acetic acid,oxalic acid, succinic acid, tartaric acid, mandelic acid, fumaric acid,lactic acid, citric acid, glutamic acid or aspartic acid. The salts thatare formed include, inter alia, hydrochlorides, hydrobromides,phosphates, carbonates, hydrogen carbonates, formates, acetates,oxalates, succinates, tartrates, fumarates, citrates and glutamates. Inthe case where the compounds of the general structure (I A), (I B)and/or (II) are acids, in particular carboxylic acids (for example ifR⁵═(CO₂H), the salt formation may be carried out by addition of a base,for example sodium hydroxide, NaHCO₃ or sodium carbonate; for the(carboxylic) acids it is particularly preferred to form the sodium salt.The particularly preferred hydrochloride formation may in particularalso be carried out by adding trimethylsilyl chloride (TMSC) to the base(I A), (I B) or (II) dissolved in a suitable organic solvent. Theformation of sodium salts may be carried out by for example titratingthe compound (I A), (I B) or (II) dissolved in a suitable solvent, forexample a water-methanol mixture, with sodium hydroxide solution.

[0300] Where the compounds of the general structure (I A), (I B) or (II)are obtained in the production process according to the invention asracemates or as mixtures of their various enantiomers and/ordiastereomers, these mixtures may be separated according to processesthat are well known in the prior art. Suitable methods include, interalia, chromatographic separation processes, in particular liquidchromatography processes under normal or elevated pressure, preferablyMPLC and HPLC processes, as well as fractional crystallisationprocesses. In this connection in particular individual enantiomers maybe separated from one another for example by means of chiral phase HPLCor by means of crystallisation of diastereomer salts formed with chiralacids, for example (+)-tartaric acid, (−)-tartaric acid or(+)-10-camphorsulfonic acid or—where acids are involved—formed withchiral bases, for example brucine or (−)-ephedrine.

[0301] Moreover the present invention also provides a medicament thatcomprises at least one of the compounds according to the invention ofthe general structure (I a), (I B) or (II) as defined above and/or theirpharmaceutically acceptable salts. In this connection the compoundsaccording to the invention may be present in the medicament according tothe invention as isomer-pure, in particular enantiomer-pure and/ordiastereomer-pure compounds, but also as a racemic or non-racemicmixture. Preferably the medicament contains a pharmaceuticallyacceptable salt of the compounds according to the invention, inparticular a hydrochloride or a sodium salt.

[0302] The present invention also provides for the use of at least onecompound according to the invention of the general structure (I A), (IB) or (II), including their diastereomers or enantiomers, also asracemates or as an enantiomer mixture, in the form of their free base oracid or in the form of a salt formed with a physiological compatibleacid or base, in particular the hydrochloride salt and sodium salt, forthe production of a medicament for pain relief. The compounds accordingto the invention have proved analgesically effective and bind to theMK801 binding site of the ionotropic NMDA receptor.

[0303] It has also been found as a result of binding to the MK801binding site that the compounds according to the invention of thegeneral structure (I A), (I B) or (II) are very suitable for treatingfurther medical conditions, in particular for treating epilepsy,schizophrenia, neurodegenerative conditions, in particular Alzheimer'sdisease, Huntington's disease and Parkinson's disease, cerebralischaemias and infarcts, psychoses due to raised amino acid levels,cerebral oedemas, insufficiency states of the central nervous system, inparticular in hypoxia and anoxia, AIDS dementia, encephalomyelitis,Tourette's syndrome, perinatal asphyxia and tinnitus. The presentapplication also provides for the use of at least one compound accordingto the invention of the general structure (I A), (I B) or (II) includinga pharmaceutically acceptable salt, for the production of a medicamentfor the treatment and/or prophylaxis of epilepsy, schizophrenia,neurodegenerative conditions, in particular Alzheimer's disease,Huntington's disease and Parkinson's disease, cerebral ischaemias andinfarcts, psychoses due to raised amino acid levels, cerebral oedemas,insufficiency states of the central nervous system, in particular inhypoxia and anoxia, AIDS dementia, encephalomyelitis, Tourette'ssyndrome, perinatal asphyxia and/or tinnitus.

[0304] It has furthermore surprisingly been shown that the compoundsaccording to the invention of the general formula (I A) and/or (I B) aresuitable ligands, in particular pharmacologically active ligands, ofnucleoside transport proteins and/or of adenosine kinase and/or ofadenosine deaminase and/or of Al and/or of A₂ and/or of A₃ receptors.

[0305] It is known that adenosine and ATP (adenosine-5′-triphosphate)and the purinergic receptors (purinoreceptors; P1 and P2 receptors)binding the latter play a significant role in the transmission andpropagation of sensory information both in peripheral nerves as well asin the dorsal horn (M. W. Salter, A. Sollevi, “Handbook of exp.pharmacol.”, Chapter 13, (2001), pp. 371-401). In particular adenosineand ATP as well as the P1 and P2 receptors play a role in thedevelopment and propagation of pain. With the P1 and P2 receptors adistinction is made between the so-called ATP receptors (=P2 receptors)and the so-called adenosine receptors (=P1 receptors). Among these P1receptors four sub-types have been identified up to the present time,namely A₁, A_(2a), A_(2b) and A₃, all of which belong to the family of Gprotein-coupled receptors (GPCR). (Hereinafter the two sub-types A_(2a)and A_(2b) will also be identified as A₂ sub-type.)

[0306] Other substances that also have an influence on the adenosinelevel in the body are adenosine kinase, which catalyses the conversionof adenosine into AMP (adenosine-5′-monophosphate), adenosine deaminase,which catalyses the hydrolytic deamination of adenosine and2′-deoxyadenosine to, respectively, inosine and 2′-deoxyinosine, and thenucleoside transport proteins, which are involved in the transport of,inter alia, adenosine from the extracellular space into the cell andvice versa. The latter play a role in particular in neuropathic painstates.

[0307] On account of the properties that have now been discovered, thepresent invention also provides for the use of compounds of the generalformula (I A) or (I B) in the form shown above or in the form of theiracid(s) or their base(s) or in the form of one of their salts, inparticular one of the physiologically compatible salts, or in the formof one of their solvates, in particular the hydrates; in the form oftheir racemate; in the form of the pure stereoisomers, in particularenantiomers or diastereomers, or in the form of mixtures of thestereoisomers, in particular of the enantiomers or diastereomers, in anarbitrary mixture ratio; in which

[0308] R¹ and R² independently of one another denote H, O—R⁹, S—R¹⁰,C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl,—(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆ alkyl)-heterocyclyl,

[0309]  in which one of the radicals R¹ and R² is H and the otherradical of R¹ and R² is not H, or in the case that one of the radicalsR¹ and R² denotes aryl, the other radical of R¹ and R² denotes H orC₁₋₁₂-alkyl,

[0310] R³ and R⁴ denote H, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl

[0311]  in which at least one of the radicals R³ and R⁴ is H, or

[0312] one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ forms W, where W denotes α′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6,α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′, α′-CH═CH—CH₂—CH₂-β′,α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, α′-O—(CH₂)_(m)-β′ where m=2,3, 4 or 5,

[0313]  the end of W identified by α′ is joined to the atom of thecompound of the general formula (I A) and/or (I B) identified by α, andthe end of W identified by β′ is joined to the atom of the compound ofthe general structure (I A) and/or (I B) identified by β, the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, and the other radical of R³and R⁴ is H or C₁₋₂-alkyl;

[0314] R⁵ denotes C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl orC(═O)R¹¹;

[0315] R⁶ denotes H, C₁₋₈-alkyl, —CN, fluorine, chlorine, bromine,iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶ where p=0, 1 or 2,—C(═O)R¹⁷ or —N═N-aryl;

[0316] R⁷ denotes H, C₁₋₈-alkyl, aryl, —CN, fluorine, chlorine, bromine,iodine, NO₂, NH₂, NHR¹², NR³R¹⁴, OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2 ordenotes C(═O)R²⁰;

[0317] R⁹ and R¹⁰ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0318] R¹¹ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl or OR²⁵;

[0319] R¹² denotes C₁₋₆-alkyl or —CH₂-aryl;

[0320] R¹³ and R¹⁴ are identical or different C₁₋₆-alkyl or togetherdenote —(CH₂)_(h)— where h=4 or 5;

[0321] R¹⁵ and R¹⁶ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0322] R¹⁷ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ or OR²⁶;

[0323] R¹⁸ and R¹⁹ independently of one another denote H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl;

[0324] R²⁰ denotes H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl or —(C₁₋₆-alkyl)-aryl or OR²⁷;

[0325] R²⁵, R²⁶, and R²⁷ independently of one another denote H orC₁₋₆-alkyl, where R²⁵ does not denote H if simultaneously R¹ denotesaryl and R² denotes alkyl;

[0326] for the prevention and/or treatment and for the production of amedicament for the prevention and/or treatment of medical conditionsand/or illnesses that are influenced via a modulation, i.e., stimulationand/or inhibition, of nucleoside transport proteins and/or of adenosinekinase and/or of adenosine deaminase and/or of A₁ and/or of A₂ and/or ofA₃ receptors.

[0327] Preferably the compounds of the general formula (1A) and/or (1B)are therefore used for the prevention and/or treatment of and for theproduction of a medicament for the prevention and/or treatment of pain,neuropathic pain, respiratory pathway conditions, cancer, cardiacarrythmias, ischaemias, epilepsy, Huntington's disease, malfunctions anddiseases of the immune system, inflammatory conditions and diseases,neonatal hypoxia, neurodegenerative conditions, Parkinson's disease,kidney failure, schizophrenia, sleep disturbances, strokes, thromboses,urinary incontinence, diabetes, psoriasis, septic shock, cerebraltrauma, glaucoma and/or congestive insufficiency. The compounds of thegeneral formulae (I A) and/or (I B) have proved effective in treatingthese conditions. In addition side effects that normally occur whenusing conventional opioid analgesics are not or are only rarely observedwith these compounds.

[0328] In addition the present invention also provides pharmaceuticalcompositions that contain at least one compound of the general structure(I A), (I B) or (II) defined above or one of their pharmaceuticallyacceptable salts and one or more pharmaceutical auxiliary substances.The medicaments and pharmaceutical compositions according to theinvention may exist and be administered as liquid, semi-solid or solidmedicament forms and in the form of for example injectable solutions,drops, juices, syrups, sprays, suspensions, granules, tablets, pellets,transdermal therapeutic systems, capsules, plasters, suppositories,ointments, creams, lotions, gels, emulsions or aerosols and, dependingon the pharmaceutical form, contain in addition to at least one compoundaccording to the invention of the general structure (I A), (I B) or(II), also pharmaceutical auxiliary substances such as for examplecarrier materials, fillers, solvents, diluents, surfactants, colourants,preservatives, release agents, intestinal lubricants, lubricants, aromasubstances and/or binders. These auxiliary substances may for example bewater, ethanol, 2-propanol, glycerol, ethylene glycol, propylene glycol,polyethylene glycol, polypropylene glycol, glucose, fructose, lactose,sucrose, dextrose, molasses, starch, modified starch, gelatin, sorbitol,inositol, mannitol, microcrystalline cellulose, methylcellulose,carboxymethylcellulose, cellulose acetate, shellac, cetyl alcohol,polyvinylpyrrolidone, paraffins, waxes, natural and synthetic gums, gumarabic, alginates, dextran, saturated and unsaturated fatty acids,stearic acid, magnesium stearate, zinc stearate, glyceryl stearate,sodium lauryl sulfate, edible oils, sesame oil, coconut oil, groundnutoil, soya bean oil, lecithin, sodium lactate, polyoxyethylene andpolyoxypropylene fatty acid esters, sorbitan fatty acid esters, sorbicacid, benzoic acid, citric acid, ascorbic acid, tannic acid, sodiumchloride, potassium chloride, magnesium chloride, calcium chloride,magnesium oxide, zinc oxide, silicon dioxide, titanium oxide, titaniumdioxide, magnesium sulfate, zinc sulfate, calcium sulfate, potassiumcarbonate, calcium phosphate, dicalcium phosphate, potassium bromide,potassium iodide, talcum, kaolin, pectin, crospovidone, agar andbentonite.

[0329] The choice of the auxiliary substances as well as the amountsthereof to be employed depends on whether the medicament is to beadministered orally, subcutaneously, parenterally, intravenously,vaginally, pulmonarily, intraperitoneally, transdermally,intramuscularly, nasally, buccally, rectally or topically, for exampleto treat infections of the skin, mucous membranes and eyes. For oraladministration, inter alia preparations in the form of tablets,sugar-coated pills, capsules, granules, drops, juices and syrups aresuitable, while for parenteral, topical and inhalative applicationsolutions, suspensions, readily reconstitutable powders for inhalationas well as sprays are suitable. Compounds according to the invention ofthe general structure (I A), (I B) or (II) in a depôt in dissolved formor in a plaster, optionally with the addition of agents promoting skinpenetration, are suitable percutaneous application preparations.Preparation forms that may be used for rectal, transmucosal, parenteraland/or percutaneous administration may provide for the delayed releaseof the compounds according to the invention of the general structure (IA), (I B) or (II).

[0330] The production of the medicaments and pharmaceutical compositionsaccording to the invention is carried out with the aid of agents,devices, methods and processes well known in the prior art relating topharmaceutical formulations, such as are described for example in“Remington's Pharmaceutical Sciences”, Ed. A. R. Gennaro, 17th Edition,Mack Publishing Company, Easton, Pa. (1985), in particular in Part 8,Chapters 76 to 93.

[0331] Thus for example for a solid formulation such as a tablet, theactive constituent of the medicament, i.e. a compound of the generalstructure (I A), (I B) or (II) or one of its pharmaceutically acceptablesalts, may be granulated with a pharmaceutical carrier, for examplecustomary tablet constituents such as maize starch, lactose, sucrose,sorbitol, talcum, magnesium stearate, dicalcium phosphate orpharmaceutically acceptable gums, and pharmaceutical diluents, such asfor example water, in order to form a solid composition that contains acompound according to the invention or a pharmaceutically acceptablesalt thereof in a state of homogeneous distribution. The expression“homogeneous distribution” is understood in the present context to meanthat the active substance is distributed uniformly throughout the wholecomposition so that the latter can be directly subdivided into equallyeffective unit-dose forms such as tablets, pills or capsules. The solidcomposition is then subdivided into unit-dose forms. The tablets orpills of the medicament according to the invention and/or of thecompositions according to the invention may also be coated or otherwisecompounded in order to provide a delayed-release dose form. Suitablecoating agents include, inter alia, polymeric acids and mixtures ofpolymeric acids with materials such as for example shellac, cetylalcohol and/or cellulose acetate.

[0332] The amount of active substance to be administered to the patientvaries and depends on the patient's weight, age and medical history, aswell as on the type of application, medical indications and severity ofthe condition.

[0333] Normally 0.1 to 5000 mg/kg, in particular 1 to 500 mg/kg andpreferably 2 to 250 mg/kg bodyweight of at least one compound accordingto the invention of the general structure (I A), (I B) or (II) areadministered.

[0334] The following examples serve to describe the present invention inmore detail:

EXAMPLES

[0335] The chemicals and solvents that were used were obtainedcommercially from one of the following suppliers: Acros, Geel; Avocado,Port of Heysham; Aldrich, Deisenhofen; Fluka, Seelze; Lancaster,Mülheim; Maybridge, Tintagel; Merck, Darmstadt; Sigma, Deisenhofen; TCI,Japan; or are prepared according to processes generally known in theprior art.

[0336] General Operating Protocol (Semi-Automated Synthesis)

[0337] A threaded round-bottom glass tube (diameter 16 mm, length 125mm) was fitted with a stirrer and sealed with a screw cap provided witha septum. The tube was placed in a stirring block adjusted to atemperature of 20° C. The following reagents were then successivelypipetted in:

[0338] 1. 1 ml of a solution containing 0.1 M trifluoroacetic acid and0.1 M heterocyclylamine component (III) or (VI), in acetonitrile

[0339] 2. 1 ml of a 0.11 M aldehyde (IV) solution in acetonitrile

[0340] 3. 1 ml of a 0.3 M olefin (V) solution in acetonitrile

[0341] The reaction mixture was stirred for 600 minutes at 20° C. in oneof the stirring blocks. The reaction solution was then filtered off atthe filtration station. The test tube was rinsed twice with 1.5 ml of a7.5% NaHCO₃ solution. The rack together with the samples was placedmanually on the working-up unit. 2 ml of diethyl ether were added to thereaction mixture in a Vortexer and shaken. The mixture was brieflycentrifuged to form a phase boundary. The phase boundary was opticallydetected and the organic phase was pipetted off.

[0342] In the next step 2 ml of diethyl ether were again added to theaqueous phase, the whole was shaken and centrifuged, and the organicphase was pipetted off. The combined organic phases were dried over 2.4g of granulated MgSO₄. The solvent was removed in a vacuum centrifuge.

[0343] Each sample was analysed by means of ESI-MS and/or NMR.

[0344] Mass spectroscopy investigations (ESI-MS) were carried out withan LCQ Classic mass spectrometer from the Finnegan company. ¹H-NMRinvestigations of the compounds according to the invention were carriedout with a 300 MHz DPX Advance NMR apparatus from Bruker.

[0345] The example compounds 1-144, 146-151 as well as 153 and 154 wereprepared according to the aforedescribed general operating protocol (seeTable 1). TABLE 1 Calculated Found Exmp. Name Mol. Wt. Mol. Wt. 13-bromo-5-(5-nitrofuran-2-yl)-7-m- 403.24 403.2/405.1tolyltetrahydropyrazolo[1,5- a]pyrimidine 23-bromo-7-(4-fluorophenyl)-7- 421.23 421.1/423.0methyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo [1,5-a]pyrimidine 33-bromo-7-naphthalin-2-yl-5-(5- 439.27 439.2/441.1nitrofuran-2-yl)-tetrahydropyrazolo [1,5-a]pyrimidine 42-(3-bromo-7-m-tolyltetrahydropyrazolo 404.31 404.5/406.4[1,5-a]pyrimidin-5-yl)- cyclopropanecarboxylic acid ethyl ester 52-[3-bromo-7-(4-bromophenyl)- 469.18 468.3/470.1/tetrahydropyrazolo[1,5-a]pyrimidin- 472.1 5-yl]-cyclopropanecarboxylicacid ethyl ester 6 2-(3-bromo-7-naphthalin-2-yl- 440.34 440.5/442.5tetrahydropyrazolo[1,5-a]pyrimidin- 5-yl)-cyclopropanecarboxylic acidethyl ester 7 3-bromo-7-(4-fluorophenyl)-7- 390.26 390.1/392.0methyl-5-(5-methylfuran-2-yl)- tetrahydropyrazolo[1,5-a]pyrimidine 83-bromo-7-(3,4-dimethoxyphenyl)- 410.27 410.3/412.2tetrahydropyrazolo[1,5-a]- pyrimidine-5-carboxylic acid ethyl ester 93-bromo-7-(4-methoxyphenyl)- 380.24 380.2/382.1tetrahydropyrazolo[1,5-a]- pyrimidine-5-carboxylic acid ethyl ester 103-bromo-7-(4-methoxyphenyl)- 352.19 354.2 tetrahydropyrazolo[1,5-a]-pyrimidine-5-carboxylic acid 11 3-bromo-7-(2,4-dimethylphenyl)-5- 417.26417.1/419.0 (5-nitrofuran-2-yl)-tetrahydropyrazolo [1,5-a]pyrimidine 123-bromo-7-(4-methoxyphenyl)-5-(5- 419.23 419.0/421.0nitrofuran-2-yl)-tetrahydropyrazolo [1,5-a]pyrimidine 135,5a,6,8a-tetrahydro-3H-1,4,8b- 305.33 306.1triaza-as-indacene-3,5-dicarboxylic acid diethyl ester; 5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as- indacene-3,5-dicarboxylic acid diethylester 14 2-hydroxy-3-phenylazo-5,5a,6,8a- 353.38 354.3tetrahydro-3H-1,4,8b-triaza-as- indacene-5-carboxylic acid ethyl ester;2-hydroxy-3-phenylazo- 5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester 152-tert.-butyl-5,5a,6,8a-tetrahydro- 289.37 290.33H-1,4,8b-triaza-as-indacene-5- carboxylic acid ethyl ester; 2-tert.-butyl-5,5a,6,8a-tetrahydro- 3H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester 16 3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-388.26 388.2/390.1 3H-1,4,8b-triaza-as-indacene- 5-carboxylic acid ethylester; 3- bromo-2-phenyl-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene- 5-carboxylic acid ethyl ester 177-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo 433.46 434.4[1,5-a]pyrimidine-3,5- dicarboxylic acid diethyl ester 183-cyano-2-methylsulfanyl-7-(2,3,4- 432.49 433.2trimethoxyphenyl)-tetrahydropyrazolo [1,5-a]pyrimidine-5- carboxylicacid ethyl ester 19 2-hydroxy-7-(4-hydroxyphenyl)-6- 421.45 422.4methyl-3-phenylazo-tetrahydropyrazolo [1,5-a]pyrimidine-5- carboxylicacid ethyl ester 20 3-bromo-7-(4-hydroxyphenyl)-6- 456.34 456.4/458.4methyl-2-phenyltetrahydropyrazolo- [1,5-a]pyrimidine-5-carboxylic acidethyl ester 21 5,5a,6,10b-tetrahydro-3H-1,4,10c- 355.39 356.2triazacyclopenta[c]fluorene-3,5- dicarboxylic acid diethyl ester;5,5a,6,10b-tetrahydro-4H-1,4,10c- triazacyclopenta[c]fluorene-3,5-dicarboxylic acid diethyl ester 22 2-hydroxy-3-phenylazo-5,5a,6,10b-403.44 404.3 tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylic acid ethyl ester; 2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-4H-1,4,10c- triazacyclopenta[c]fluorene-5-carboxylic acid ethyl ester 23 7-phenylsulfanyltetrahydropyrazolo-375.44 376.2 [1,5-a]pyrimidine-3,5-dicarboxylic acid diethyl ester 243-cyano-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo 374.48 375.1[1,5- a]pyrimidine-5-carboxylic acid ethyl ester 253-cyano-2-methylsulfanyl-7-(2,3,4- 404.44 405.2trimethoxyphenyl)-tetrahydropyrazolo [1,5-a]pyrimidine-5- carboxylicacid 26 7-phenylsulfanyltetrahydropyrazolo- 347.39 348.2[1,5-a]pyrimidine-3,5-dicarbaxylic acid-3-ethyl ester 273-cyano-7-(2,4-dimethylphenyl)-2- 370.47 371.2methylsulfanyl-tetrahydropyrazalo- [1,5-a]pyrimidine-5-carboxylic acidethyl ester 28 3-cyano-7-(2,4-dimethylphenyl)- 324.38 325.2tetrahydropyrazolo[1,5-a]- pyrimidine-5-carboxylic acid ethyl ester 297-(2,4-dimethylphenyl)-tetrahydropyrazolo 343.38 344.2[1,5-a]pyrimidine-3,5- dicarboxylic acid-3-ethyl ester 303-bromo-7-(2,4-dimethylphenyl)-2- 426.31 426.2/428.1phenyltetrahydropyrazolo-[1,5-a]- pyrimidine-5-carboxylic acid 313-cyano-7-(2,4-dimethylphenyl)-2- 342.42 343.2methylsulfanyltetrahydropyrazolo[1, 5-a]pyrimidine-5-carboxylic acid 323-cyano-7-(2,4-dimethylphenyl)- 296.32 297.2 tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid 33 3-cyano-7-(3,4-dimethoxyphenyl)-2-374.41 376.2 methylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 34 7-(2,4-dimethylphenyl)-5-(5- 410.42411.1 nitrofuran-2-yl)tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylicacid ethyl ester 35 7-(2,4-dimethylphenyl)-5-(5- 458.47 459.3nitrofuran-2-yl)-3-phenylazotetrahydropyrazolo [1,5-a]pyrimidin-2-ol 363-bromo-7-(2,4-dimethylphenyl)-5- 493.36 493.2/495.1(5-nitrofuran-2-yl)-2-phenylazotetrahydropyrazolo [1,5-a]pyrimidine 377-(2,4-dimethylphenyl)-2-methylsulfanyl- 409.46 410.15-(5-nitrofuran-2-yl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 38 7-(2,4-dimethylphenyl)-5-(5- 363.37 364.1nitrofuran-2-yl)-tetrahydropyrazolo [1,5-a]pyrimidine-3- carbonitrile 393-bromo-7-(3,4-dimethoxyphenyl)-5- 525.36 525.4/527.1(5-nitrofuran-2-yl)-2-phenyl- tetrahydropyrazolo[1,5-a]pyrimidine 407-(4-methoxyphenyl)-2-methylsulfanyl- 411.43 412.95-(5-nitro-furan-2-yl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 41 7-(2,4-dimethylphenyl)-5-(2- 411.5 412.5ethoxycarbonylcyclo-propyl)- tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 422-[7-(2,4-dimethylphenyl)-2- 459.54 460.3hydroxy-3-phenylazotetrahydropyrazolo [1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 432-[2-tert.-butyl-7-(2,4-dimethylphenyl) 395.54 396.5tetrahydropyrazolo[1,5- a]pyrimidin-5-yl]cyclopropanecarboxylic acidethyl ester 44 2-[3-bromo-7-(2,4-dimethylphenyl)- 494.43 494.4/496.22-phenyltetra-hydropyrazolo[1,5- a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester 45 2-[3-cyano-7-(2,4-dimethylphenyl)- 410.53 411.32-methylsulfanyltetrahydropyrazolo-[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 465-(2-ethoxycarbonylcyclopropyl)-7- 401.43 402.2(3-fluorophenyl)tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester 47 2-[3-bromo-7-(3-bromophenyl)-2- 545.28 544.3/546.1/phenyltetrahydropyrazolo[1,5-a]- 548.0pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 482-[7-(3-bromophenyl)-3-cyano-2- 461.38 461.2/463.0methylsulfanyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 497-(2,4-dimethylphenyl)-5-(5- 474.54 475.2nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo [1,5-a]pyrimidin- 2-ol50 7-(2,4-dimethylphenyl)-2-methyl- 425.53 426.1sulfanyl-5-(5-nitrothiophen-2-yl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 51 7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-379.44 380.1 2-yl)-tetrahydropyrazolo- [1,5-a]pyrimidine-3-carbonitrile52 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen- 458.49 459.32-yl)-tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acid ethylester 53 7-(3,4-dimethoxyphenyl)-5-(5- 506.54 507.2nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo [1,5-a]pyrimidin- 2-ol54 3-bromo-7-(3,4-dimethoxyphenyl)-5- 541.42 541.4/543.3(5-nitrothiophen-2-yl)-2-phenyltetrahydropyrazolo [1,5-a]pyrimidine 557-(3,4-dimethoxyphenyl)-2-methylsulfanyl- 457.53 458.15-(5-nitrothiophen-2-yl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 56 7-(3,4-dimethoxyphenyl)-5-(5- 411.43 412.1nitrothiophen-2-yl)- tetrahydropyrazolo[1,5- a]pyrimidine-3-carbonitrile57 7-(4-methoxyphenyl)-5-(5-nitrothiophen- 428.46 429.12-yl)-tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acid ethylester 58 5-[3-bromo-7-(4-methoxyphenyl)-2- 494.34 494.2/496.1phenyltetrahydropyrazolo[1,5-a]- pyrimidin-5-yl]-furan-2-carboxylic acid59 5-benzoyl-7-(2,4-dimethylphenyl)- 403.48 404.2tetrahydropyrazolo-[1,5-a]- pyrimidine-3-carboxylic acid ethyl ester 605-benzoyl-7-(2,4-dimethylphenyl)-2- 402.51 403.1methylsulfanyltetrahydropyrazolo[1, 5-a]pyrimidine-3-carbonitrile 615-benzoyl-7-(2,4-dimethylphenyl)- 356.42 355.3/357.2tetrahydropyrazolo-[1,5-a]- pyrimidine-3-carbonitrile 625-benzoyl-7-(3,4-dimethoxyphenyl)- 435.47 436.2tetrahydropyrazolo[1,5-a]- pyrimidine-3-carboxylic acid ethyl ester 63[3-bromo-7-(3,4-dimethoxyphenyl)-2- 518.41 518.7/520.2phenyltetrahydro-pyrazolo[1,5-a]- pyrimidin-5-yl]phenylmethanone 645-benzoyl-7-(3,4-dimethoxyphenyl)- 434.51 435.12-methylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carbonitrile 655-benzoyl-7-(3,4-dimethoxyphenyl)- 388.42 389.1tetrahydropyrazolo[1,5-a]- pyrimidine-3-carbonitrile 665-benzoyl-7-(4-methoxyphenyl)- 405.45 406.1 tetrahydropyrazolo-[1,5-a]-pyrimidine-3-carboxylic acid ethyl ester 675-benzoyl-7-(4-methoxyphenyl)-2- 404.49 405.0methylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carbonitrile 685-benzoyl-7-(4-methoxyphenyl)tetrahydropyrazolo- 358.4 359.0[1,5-a]pyrimidine-3- carbonitrile 69 5-benzoyl-7-(3-fluorophenyl)-393.41 394.4 tetrahydropyrazolo-[1,5-a]- pyrimidine-3-carboxylic acidethyl ester 70 [3-bromo-7-(3-fluorophenyl)-2- 476.35 476.3/478.3phenyltetrahydropyrazolo[1,5-a]- pyrimidin-5-yl]-phenylmethanone 71[3-bromo-7-(3-bromophenyl)-2- 537.26 538.4phenyltetrahydro-pyrazolo[1,5-a]- pyrimidin-5-yl]phenylmethanone 727-(2,4-dimethylphenyl)-5-(4- 467.56 468.2phenoxyphenyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester 73 3-bromo-7-(2,4-dimethylphenyl)-5- 550.5 550.3/552.2(4-phenoxyphenyl)-2- phenyltetrahydro-pyrazolo[1,5- a]pyrimidine 747-(2,4-dimethylphenyl)-2-methylsulfanyl- 466.6 467.15-(4-phenoxyphenyl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 75 7-(2,4-dimethylphenyl)-5-(4- 420.51 421.1phenoxyphenyl)tetrahydropyrazolo- [1,5-a]pyrimidine-3-carbonitrile 767-(3,4-dimethoxyphenyl)-5-(4- 499.56 500.2phenoxyphenyl)tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester 77 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl- 498.6 499.15-(4-phenoxyphenyl)- tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 78 3-[3-cyano-7-(4-hydroxyphenyl)-6- 390.39391.1 methyltetrahydropyrazolo[1,5-a]- pyrimidin-5-yl]-2-hydroxybenzoicacid 79 3-(3-cyano-5,5a,6,10b-tetrahydro- 372.38 373.03H-1,4,10c-triazacyclopenta[c]- fluoren-5-yl)-2-hydroxybenzoic acid;3-(3-cyano-5,5a,6,10b- tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoic acid 803-(3-cyano-7-phenylsulfanyltetra- 392.43 392.9hydropyrazolo[1,5-a]pyrimidin-5- yl]-2-hydroxybenzoic acid 813-[2-tert.-butyl-7-(4-chloro-phenyl)- 439.94 440.27-methyltetrahydropyrazolo- [1,5-a]pyrimidin-5-yl]-2-hydroxybenzoic acid82 5-(4-hydroxy-3-methoxyphenyl)-7-(4- 423.46 424.1hydroxyphenyl)-6-methyltetrahydropyrazolo [1,5-a]pyrimidine-3-carboxylic acid ethyl ester 83 5-(4-hydroxy-3-methoxyphenyl)-7-(4-376.41 377.1 hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3- carbonitrile 84 5-(4-hydroxy-3-methoxyphenyl)-405.45 406.0 5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3- carboxylic acid ethyl ester; 5-(4-hydroxy-3-methoxyphenyl)- 5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3- carboxylic acid ethyl ester 854-(2-tert.-butyl-5,5a,6,10b- 389.49 390.2 tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2- methoxyphenol; 4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-4H-1,4,10c- triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol 86 5-(4-hydroxy-3-methoxyphenyl)-2- 404.49 404.9methylsulfanyl-5,5a,6,10b- tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile; 5- (4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b- tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3- carbonitrile 875-(4-hydroxy-3-methoxyphenyl)-7- 425.5 426.0phenylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester 88 4-(2-tert.-butyl-7-phenylsulfanyltetrahydro- 409.55 410.1pyrazolo[1,5-a]- pyrimidin-5-yl)-2-methoxyphenol 894-(3-bromo-2-phenyl-7-phenylsulfanyl- 508.44 508.2/510.0tetrahydro-pyrazolo[1,5- a]pyrimidin-5-yl)-2-methoxyphenol 905-(2-hydroxy-3-methoxyphenyl)-7- 425.5 425.0phenylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester 91 7-(4-chlorophenyl)-5-(2-hydroxy-3- 441.91 441.0methoxyphenyl)-7-methyltetrahydropyrazolo [1,5-a]pyrimidine-3-carboxylic acid ethyl ester 92 5-(4-hydroxybutyl)-5,5a,6,10b- 308.38309.3 tetrahydro-3H-1,4,10c-triazacyclopenta [c]fluorene-3-carbonitrile;5- (4-hydroxybutyl)-5,5a,6,10b-tetrahydro- 4H-1,4,10c-triazacyclopenta-[c]fluorene-3-carbonitrile 93 5-(4-hydroxybutyl)-2-methylsulfanyl-374.52 375.2 7-phenyl-sulfanyltetrahydropyrazolo [1,5-a]pyrimidine-3-carbonitrile 94 5-(4-hydroxybutyl)-7-phenylsulfanyltetrahydro- 328.43329.2 pyrazolo[1,5- a]pyrimidine-3-carbonitrile 957-(4-chlorophenyl)-5-(4- 344.84 345.1hydroxybutyl)-7-methyltetrahydropyrazolo [1,5-a]pyrimidine-3-carbonitrile 96 5-butyl-2-methylsulfanyl- 338.47 339.35,5a,6,10b-tetrahydro-3H-1,4,10c- triazacyclopenta[c]fluorene-3-carbonitrile; 5-butyl-2-methylsulfanyl- 5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]- fluorene-3-carbonitrile 975-butyl-2-methylsulfanyl-7- 358.52 359.2phenylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidine-3-carbonitrile 985-butyl-7-phenylsulfanyltetrahydropyrazolo 312.43 313.1[1,5-a]pyrimidine-3- carbonitrile 99 5-butyl-7-(4-chlorophenyl)-7-374.93 375.3 methylsulfanyltetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile 1005-cyclopropyl-7-(2,4-dimethylphenyl)- 387.48 388.53-phenylazotetrahydro- pyrazolo[1,5-a]pyrimidin-2-ol 1012-tert.-butyl-5-cyclopropyl-7-(2,4- 323.48 324.6dimethylphenyl)-tetrahydropyrazolo- [1,5-a]pyrimidine 1025-cyclopropyl-7-(2,4-dimethylphenyl)- 338.47 339.82-methylsulfanyltetrahydropyrazolo [1,5-a]-pyrimidine-3- carbonitrile103 2-tert.-butyl-5-cyclopropyl-7-(3,4- 355.48 356.3/357.6dimethoxyphenyl)tetrahydropyrazolo- [1,5-a]pyrimidine 1043-bromo-5-cyclopropyl-7-(3,4- 454.37 454.3/456.1dimethoxyphenyl)-2-phenyltetrahydropyrazolo [1,5-a]pyrimidine 1055-cyclopropyl-7-(4-methoxyphenol)- 341.41 342.7tetrahydropyrazolo[1,5-a]- pyrimidine-3-carboxylic acid ethyl ester 1065-cyclopropyl-3,5,5a,6,7,11b- 290.36 291.4hexahydro-1,4,11c-triazacyclopenta- [c]phenanthrene-3-carbonitrile 1077-(2,4-dimethylphenyl)-5-pyridin-2- 376.45 377.3/378.4yl-tetrahydro-pyrazolo[1,5-a]- pyrimidine-3-carboxylic acid ethyl ester108 7-(2,4-dimethylphenyl)-3-phenylazo- 424.5 425.35-pyridin-2-yl-tetrahydropyrazolo- [1,5-a]pyrimidin-2-ol 1093-bromo-7-(2,4-dimethylphenyl)-2- 459.39 459.7/462.2phenyl-5-pyridin-2-yl-tetrahydropyrazolo [1,5-a]pyrimidine 1107-(2,4-dimethylphenyl)-2-methylsulfanyl- 375.49 376.45-pyridin-2-yl-tetrahydropyrazolo [1,5-a]pyrimidine-3- carbonitrile 1117-(3,4-dimethoxyphenyl)-2-methylsulfanyl- 434.56 435.35-phenethyl-tetrahydropyrazolo [1,5-a]pyrimidine-3- carbonitrile 1127-(3,4-dimethoxyphenyl)-5- 388.47 389.2phenethyltetrahydropyrazolo[1,5-a]- pyrimidine-3-carbonitrile 1135-cyclopropyl-7-(2-hydroxyethoxy)- 295.33 296.2 tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 1142-(2-tert.-butyl-5-cyclopropyltetrahydropyrazolo- 279.38 280.3 [1,5-a]-pyrimidin-7-yloxy)-ethanol 115 5-cyclopropyl-3,5,5a,6,7,8a- 277.32 278.3hexahydro-8-oxa-1,4,8b-triaza-as- indacene-3-carboxylic acid ethylester; 5-cyclopropyl-4,5,5a,6,7,8a- hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester 116 5-cyclopropyl-3-phenylazo-325.37 326.5 3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol; 5- cyclopropyl-3-phenylazo-4,5,5a,6,7,8a-hexahydro-8-oxa- 1,4,8b-triaza-as-indacen-2-ol 1177-cyclohexyloxy-5-cyclopropyltetrahydropyrazolo 333.43 334.1[1,5-a]pyrimidin-3- carboxylic acid ethyl ester 1187-cyclohexyloxy-5-cyclopropyl-2- 332.46 333.2methylsulfanyltetrahydropyrazolo- [1,5-a]pyrimidin-3-carbonitrile 1197-(4-chlorophenyl)-5-cyclohexyltetrahydropyrazolo- 340.85 341.4[1,5-a]pyrimidin- 3-carbonitrile 120 5-cyclohexyl-7-(2-hydroxyethoxy)-337.41 338.3 tetrahydropyrazolo[1,5-a]- pyrimidine-3-carboxylic acidethyl ester 121 5-cyclohexyl-3,5,5a,6,7,8a- 319.4 320.3hexahydro-8-oxa-1,4,8b-triaza-as- indacene-3-carboxylic acid ethylester; 5-cyclohexyl-4,5,5a,6,7,8a- hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester 1225-cyclohexyl-7-cyclohexyloxytetrahydropyrazolo- 375.51 376.2 [1,5-a]-pyrimidine-3-carboxylic acid ethyl ester 1237-(2,4-dimethylphenyl)-3-phenylazo- 389.5 390.55-propyl-tetrahydropyrazolo[1,5-a]- pyrimidin-2-ol 1247-(2,4-dimethylphenyl)-2-methylsulfanyl- 340.49 341.35-propyltetrahydropyrazolo [1,5-a]pyrimidine-3- carbonitrile 1255-tert.-butyl-7-(2,4-dimethylphenyl)- 355.48 356.1tetrahydropyrazolo[1,5-a]- pyrimidine-3-carboxylic acid ethyl ester 1262,5-di-tert.-butyl-7-(3,4- 371.52 372.2dimethoxyphenyl)tetrahydropyrazolo- [1,5-a]pyrimidine 1273-bromo-5-tert.-butyl-7-(3,4- 470.41 470.2/472.1dimethoxyphenyl)-2-phenyltetrahydropyrazolo [1,5-a]pyrimidine 1282-[3-cyano-6,7-bis-(4- 472.54 473.0 methoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 1293-cyano-6,7-bis-(4-methoxyphenyl)- 404.42 405.0tetrahydro-pyrazolo[1,5-a]- pyrimidine-5-carboxylic acid 1304-[3-bromo-6-methyl-2-phenyl-5-(4- 528.37 528.1trifluoromethylphenyl)tetrahydropyrazolo [1,5-a]pyrimidin-7-yl]- phenol131 7-(4-hydroxyphenyl)-6-methyl-2- 444.47 445.1methylsulfanyl-5-(4-trifluoromethylphenyl) tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile 132 7-(4-hydroxyphenyl)-6-methyl-5-(4-398.38 399.1 trifluoromethylphenyl)tetrahydropyrazolo[1,5-a]pyrimidine-3- carbonitrile 133 2-(4-nitrophenylsulfonyl)-5-510.61 511.2 phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]- pyrimidine 1343-(4-chlorophenyl)-5-phenylsulfanyl- 435.99 436.4 7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]- pyrimidine 1355-phenylsulfanyl-7-pyridin-2-yl-3- 415.58 416.3 p-tolyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine 136 7-methoxy-4-phenylsulfanyl-2- 405.54 406.3pyridin-2-yl-3,4-dihydro-2H-9-thia- 1,4a-diazafluorene 1377-ethoxy-4-phenylsulfanyl-2- 419.56 420.3pyridin-2-yl-3,4-dihydro-2H-9-thia- 1,4a-diazafluorene 1387-fluoro-4-phenylsulfanyl-2- 393.5 394.2pyridin-2-yl-3,4-dihydro-2H-9-thia- 1,4a-diazafluorene 1393-naphthalin-2-yl-5-phenylsulfanyl- 451.61 452.57-pyridin-2-yl-6,7-dihydro-5H- thiazolo[3,2-a]pyrimidine 1407-phenyl-3-phenylazo-5-pyridin-2- 396.47 397.4yl-3,5,6,7-tetrahydropyrazolo[1,5- a]pyrimidin-2-ol 1417-phenylsulfanyl-5-pyridin-2-yl- 380.5 381.43,5,6,7-tetrahydropyrazolo[1,5- a]pyrimidine-3-carboxylic acid ethylester 142 3-phenylazo-7-phenylsulfanyl-5- 428.51 429.6pyridin-2-yl-3,5,6,7-tetrahydropyrazolo [1,5-a]pyrimidin-2-ol 1433-bromo-7-phenylsulfanyl-5-pyridin- 387.3 387.22-yl-3,5,6,7-tetrahydropyrazolo- [1,5-a]pyrimidine 1447-phenylsulfanyl-5-pyridin-2-yl- 333.41 334.23,5,6,7-tetrahydropyrazolo[1,5-a]- pyrimidine-3-carbonitrile 1467-(3,4-dimethoxyphenyl)-2-methylsulfanyl- 407.0 409.5/409.95-pyridin-2-yl-tetrahydropyrazolo [1,5-a]pyrimidine-3- carbonitrile 1473-bromo-7-(3,4-dimethoxyphenyl)-2- 490.9 492.6/494.4phenyl-5-pyridin-2-yl-tetrahydropyrazolo [1,5-a]pyrimidine 1483-bromo-7-(3,4-dimethoxyphenyl)-2- 485.9 486.5/488.4phenyltetrahydro-pyrazolo[1,5- a]pyrimidine-5-carboxylic acid ethylester 149 3-bromo-7-(3,4-dimethoxyphenyl)-5- 524.9 525.4/527.1(5-nitrofuran-2-yl)-2-phenyl- tetrahydropyrazolo[1,5-a]pyrimidine 1503-cyano-7-(3,4-dimethoxyphenyl)-2- 402.0 402.5methylsulfanyltetrahydropyrazolo[1, 5-a]pyrimidine-5-carboxylic acidethyl ester 151 3-cyano-7-(3,4-dimethoxyphenyl)- 356.0 357.2tetrahydropyrazolo-[1,5-a]- pyrimidine-5-carboxylic acid ethyl ester 1537-(3,4-dimethoxyphenyl)-2- 441.5 442.1 methylsulfanyl-5-(5-nitrofuran-2-yl) tetrahydropyrazolo[1,5-a]- pyrimidine-3-carbonitrile 1547-(3,4-dimethoxyphenyl)-5-pyridin- 408.5 409.52-yl-4,5,6,7-tetrahydropyrazolo- [1,5-a]pyrimidine-3-carboxylic acidethyl ester

Example 145

[0346]3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidineDihydrochloride

[0347] 1.5 g of 5-amino-4-bromo-3-phenylpyrazole in acetonitrile wereplaced in a 100 ml single-necked flask, and 1.55 g of3,4-dimethoxystyrene, 0.88 g of 2-pyridyl carbaldehyde and 0.72 ml oftrifluoroacetic acid were added and the whole was stirred overnight atroom temperature. The reaction solution was completely concentrated byevaporation. The crude product was purified by reversed phase HPLC. HPLCcolumn: Macherey-Nagel, VP 100/21 Nucleosil 100-3 C18 HD (serial no.0115186 batch 23710123):

[0348] Gradient: methanol (Riedel-de-Haen, Chromasolv)/water: gradient(4 stages) from 60% to 100% methanol in 37.5 minutes (flow rate 10ml/min, injection volume: 1 ml) HPLC: Beckman SYSTEM GOLD, (Detector166, Injector Endurance/SPARK, 125P Solvent Module, fraction collector:Foxy200/ISCO)

[0349] To form the hydrochloride 139 mg of3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidinewere dissolved in 1.1 ml of methyl ethyl ketone and then 6 μl of H₂O and7 μl of TMSCl were added. After some time a solid precipitated out.After suction filtration and washing with ether, yellow crystals wereobtained that were dried under a vacuum.

[0350]¹H-NMR data (600 MHz; DMSO-d6):

[0351] δ=8.68 (m, 1H), 8.27 (m, 1H), 7.92 (d, 1H, J=8.1 Hz), 7.74-7.67(m, 3H), 7.39 (dd, 2H, J=7.5, 7.5 Hz), 7.33 (t, 1H, J=7.2 Hz), 6.83 (d,1H, J=7.7 Hz), 6.78 (s, 1H), 6.66 (d, 1H, J=9.0 Hz), 5.47 (m, 1H), 5.03(m, 1H), 3.71 (s, 3H), 3.69 (s, 3H), 2.67 (m, 1H), 2.59 (m, 1H)

Example 147

[0352]3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine,prepared according to the process described above

[0353]¹H-NMR data (600 MHz; DMSO-d6):

[0354] δ=8.34 (br. s, 1H), 7.93 (d, 1H, J=3.8 Hz), 7.64 (s, 1H), 7.14(d, 1H, J=4.5 Hz), 6.81 (d, 1H, J=8.3 Hz), 6.71 (s, 1H) 6.60 (d, 1H,J=8.3 Hz), 5.40 (dd, 1H J=4.5, 8.3 Hz), 5.09 (br. d, 1H, J=8.3 Hz), 3.70(s, 3H), 3.68 (s, 3H), 2.59 (br. d, 1H, J=13.6 Hz), 2.50 (m, 1H).

Example 152

[0355]7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrileDihydrochloride

[0356] 1 g (9.3 mmoles) of 3-aminopyrazole-4-carbonitrile was placed in28 ml of acetonitrile, and 2.28 g (13.9 mmoles) of 3,4-dimethoxystyrene,1.29 g (12 mmoles) of pyridine-2-carbaldehyde and 1.05 g (9.3 mmoles) oftrifluoroacetic acid were added and the whole was stirred overnight atroom temperature. The dark brown solution was completely concentrated byevaporation in a rotary evaporator and dried. The product was purifiedby HPLC (conditions as described above).

[0357] The base that was thereby obtained (270 mg) was suspended inmethanol and 15 μl of H₂O and 208 μl of TMSCl were then added. A clearsolution was formed which was concentrated by evaporation on aRotavapor. The yellow crystals that were formed were dried under avacuum.

[0358]¹H-NMR data (600 MHz; DMSO-d6):

[0359] δ=8.65 (d, 1H, J=4.8 Hz), 8.23 (t, 1H, J=7.2 Hz), 8.16 (m, 1H),7.86 (d, 1H), 7.70-7.65 (m, 2H), 6.77 (d, 1H, J=8.3 Hz) 6.68 (s, 1H),6.53 (d, 1H, J=8.3 Hz), 5.43 (dd, 1H, J=4.5, 7.5 Hz), 5.08 (m, 1H), 3.70(s, 3H), 3.68 (s, 3H), 2.73 (m, 1H), 2.63 (br. d, 1H, J=14.3 Hz)

Example 56 Dihydrochloride

[0360] The dihydrochloride of7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrilewas prepared in a similar manner to Examples 145 and 152.

[0361]¹H-NMR data (600 MHz; DMSO-d6):

[0362] δ=8.65 (d, 1H, J=4.8 Hz), 8.23 (t, 1H, J=7.2 Hz), 8.16 (m, 1H),7.86 (d, 1H), 7.70-7.65 (m, 2H), 6.77 (d, 1H, J=8.3 Hz) 6.68 (s, 1H),6.53 (d, 1H, J=8.3 Hz), 5.43 (dd, 1H, J=4.5, 7.5 Hz), 5.08 (m, 1H), 3.70(s, 3H), 3.68 (s, 3H), 2.73 (m, 1H), 2.63 (br. d, 1H, J=14.3 Hz).

[0363] Pharmacological Investigations:

[0364] The investigations to determine the NMDA antagonistic action ofthe compounds according to the invention were carried out on brainmembrane homogenates (rat brain homogenate minus cerebellum, pons andmedulla oblongata from male Wistar strain rats (Charles River, Sulzfeld,Germany)).

[0365] For this, freshly prepared rat brains were digested, afterremoval of the cerebellum, pons and medulla oblongata, in 50 mmole/lTris/HCl (pH 7.7) in a Polytron homogeniser (model PT3000, KinematikaAG, Littau, Switzerland) at 6,000 revs. per minute (rpm) for 1 minutewhile cooling in ice and then centrifuged for 15 minutes at 4° C. and60,000 g.

[0366] The supernatant was decanted and discarded, and the membranepellet was taken up again in 50 mmole/l of Tris/HCl (pH 7.7) anddigested in a homogeniser at 2,000 rpm for 1 minute and recentrifugedfor 15 minutes at 4° C. and 60,000 g. The supernatant was discardedagain and the membrane pellet was homogenised in 50 mmole/l Tris/HCl (pH7.7) (2,000 rpm for 1 minute) and aliquot portions were frozen at −70°C.

[0367] For the receptor binding test aliquots were in each case thawedout and then centrifuged for 15 minutes at 4° C. and 60,000 g. Afterdecanting and discarding the supernatant, the membrane pellet for thebinding test was taken up in binding test buffer and homogenised (2,000rpm for 1 minute). 5 mmole/l Tris/HCl (pH 7.7) supplemented with 30μmole/l of glycine and 100 μmole/l of glutamic acid was used as bindingtest buffer.

[0368] 1 nmole/l of (³H)-(+)-MK801 ((5R,10S)-(+)-5-methyl-10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5,10-imine(NET-972, NEN, Cologne, Germany) was added as radioactively labelledligand. The proportion of non-specific binding was determined in thepresence of 10 μmole/l of non-radioactively labelled (+)-MK801(RBI/Sigma, Deisenhofen, Germany). In further assays the respectivecompounds according to the invention were added in concentration seriesand the displacement of the radioactive ligand from its specific bindingto the NMDA receptor was measured.

[0369] The batches were incubated in each case for 40 minutes at 25° C.and then harvested by filtration to determine the radioactive ligandbound to the brain membrane homogenate. The radioactivity retained bythe filter was measured after adding a scintillator (“Ready Protein”scintillator, Beckmann Coulter GmbH, Krefeld, Germany) in a β-counter(Packard TR¹-CARB Liquid Scintillation Analyser 2000CA, PackardInstrument, Meriden, Conn. 06450, USA).

[0370] The resulting percentage inhibition of the specific binding ofthe ligand (³H)-(+)-MK801 in the presence of in each case 10 μmole/l ofthe respective compound according to the invention serves as a measureof the affinity of this compound for the (+)-MK801 binding site of theionotropic NMDA receptor. The affinities are given in Table 2 as meanvalues of double determinations on selected examples. TABLE 2 Example %Inhibition 140 44 141 45 142 75 143 49 144 45

[0371] The following test conditions were chosen for the determinationof the inhibition of the nucleoside transport protein:

[0372] 100 μl of the substance solution in aqueous solution with DMSO assolution aid were incubated for 30 minutes at 25° C. with 100 μl of 1.5nM [³H]NBl (N⁶-benzyladenosine), 100 μl of buffer (50 mM Tris.HCl, pH7.4) and 100 μl of an aqueous suspension of erythrocyte membrane. Afterthe incubation the test mixture was filtered off (Whatman GF/C Filter,post-washed with 50 mM Tris.HCl). The filters were transferred to testtubes, 3.5 ml of scintillation fluid were added, and after 2 hours theradioactivity was measured in a β-counter. The measurement results (Kivalue at 10 μM and % displacement at 10 μM) are shown in Table 3. TABLE3 % Displacement at Example No. K_(i) Value [μM] 10 μM 39 40 53 0.6 541.3 55 0.4 56 43 64 0.6 111 0.3 145 0.4 153 50 154 41

[0373] The dihydrochloride of Example 147 (prepared from Example 147 ina similar manner to Examples 145 and 152) was investigated as regardsits affinity for the recombinant human adenosine A₃ receptor in adisplacement assay (C. A. Salvatore et al., Process. Natl. Acad. Sci.USA (1993), Vol. 90, 10365-10369). At a ligand concentration of 0.1 nM[¹²⁵I]AB-MECA (N⁶-(4-amino-3-[¹²⁵I]iodobenzyladenosine) the displacementat a concentration of 3 μM was 93%.

[0374] Pharmaceutical Formulation of a Medicament According to theInvention

[0375] 1 g of the hydrochloride of3-phenylazo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-olwas dissolved at room temperature in 1 l of water for injection purposesand then adjusted to isotonic conditions by addition of sodium chloride.

[0376] The foregoing description and examples have been set forth merelyto illustrate the invention and are not intended to be limiting. Sincemodifications of the described embodiments incorporating the spirit andsubstance of the invention may occur to persons skilled in the art, theinvention should be construed broadly to include all variations withinthe scope of the appended claims and equivalents thereof.

What is claimed is:
 1. A compound corresponding to the structure (I A),(I B) or (II)

or a salt thereof, or a solvate or hydrate thereof, or a stereoisomer,mixture of stereoisomers having an arbitrary mixture ratio, or a racemicmixture thereof; wherein R¹ and R² are independently selected from thegroup consisting of H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆alkyl)-heterocyclyl,  wherein exactly one of the radicals R¹ and R² isH, or wherein one of the radicals R¹ and R² is aryl and the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, R³ and R⁴ are selected fromthe group consisting of H, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl, wherein at least oneof the radicals R³ and R⁴ is H, or one of the radicals R¹ and R²together with one of the radicals R³ and R⁴ form W, where W isα′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6, α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′,α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, orα′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified bya in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β′ in thecompound corresponding to structure (I A), (I B) or (II), the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, and the other radical of R³and R⁴ is H or C₁₋₁₂-alkyl; R⁵ is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆alkyl)-heterocyclyl or C(═O)R¹¹; R⁶ is H, C₁₋₈-alkyl, —CN, fluorine,chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶where p=0, 1 or 2, —C(═O)R¹⁷ or —N═N-aryl; R⁷ is H, C₁₋₈-alkyl, aryl,—CN, fluorine, chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴,OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2, or C(═O)R²⁰, R⁸ is H, C₁₋₈-alkyl oraryl, or R⁷ and R⁸ together form Y, wherein Y is γ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ′ is joined to the atomidentified by γ in the compound corresponding to structure (II), andwhere the end of Y identified by δ′ is joined to the atom identified byδ in the compound corresponding to structure (II); R⁹ and R¹⁰ areindependently selected from the group consisting of H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and —(C₁₋₆-alkyl)-aryl; R¹¹is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵;R¹² is C₁₋₆-alkyl or —CH₂-aryl; R¹³ and R¹⁴ are identical or differentC₁₋₆-alkyl radicals, or together are —(CH₂)_(h)— and form a ring, whereh=4 or 5; R¹⁵ and R¹⁶ are independently selected from the groupconsisting of H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryland —(C₁₋₆-alkyl)-aryl; R¹⁷ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ orOR²⁶; R¹⁸ and R¹⁹ are independently selected from the group consistingof H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and—(C₁₋₆-alkyl)-aryl; R²⁰ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl or OR²⁷; R²¹, R²², R²³and R²⁴ are independently selected from the group consisting of H,fluorine, chlorine, bromine, iodine and OR²⁸; R²⁵, R²⁶, R²⁷ and R²⁸ areindependently selected from the group consisting of H and C₁₋₆-alkyl,where R²⁵ is not H when both R¹ is aryl and R² is alkyl; and wherein thecompound is not4,5,6,7-tetrahydro-2-methyl-5,7-diphenylpyrazolo-[1,5-a]pyrimidine,4,5,6,7-tetrahydro-2,5-dimethyl-7-phenylpyrazolo-[1,5-a]pyrimidine,4,5,6,7-tetrahydro-5,7-dimethyl-3-phenylpyrazolo-[1,5-a]pyrimidine,4,5,6,7-tetrahydro-2,5,7-trimethylpyrazolo[1,5-a]pyrimidine,4,5,6,7-tetrahydro-5,7-dimethyl-2-phenylpyrazolo-[1,5-a]pyrimidine,4,5,6,7-tetrahydro-2-methyl-5,7-di-n-propylpyrazolo[1,5-a]pyrimidine-3-carbonitrile,4,5,6,7-tetrahydro-5-methyl-7-[3-(trifluoromethyl)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile,7-[4-(chloro)-phenyl]-4,5,6,7-tetrahydro-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile,7-[3-(chloro)-phenyl]-4,5,6,7-tetrahydro-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile,3,4-dihydro-2-(4-nitrophenyl)-4-phenyl-2H-pyrimido[2,1-b]benzothiazole,or3,4-dihydro-4-(4-methylphenyl)-2-(4-nitrophenyl)-2H-pyrimido[2,1-b]benzothiazole.2. A compound according to claim 1, wherein the compound is present as aphysiologically compatible salt.
 3. A compound according to claim 1,wherein the compound is present as a pure enantiomer or a purediastereomer.
 4. A compound according to claim 1, wherein the compoundis present as a mixture of enantiomers or a mixture of stereoisomers. 5.A compound according to claim 1, wherein R¹ and R² are independentlyselected from the group consisting of H, O—R⁹, S—R¹⁰, C₁₋₆-alkyl, aryl′or —(C₁₋₆-alkyl)-aryl′, wherein aryl′ is aryl¹, aryl², or aryl³,

 wherein exactly one of the radicals R¹ and R² is H, or wherein one ofthe radicals R¹ and R² is aryl′ and the other radical of R¹ and R² is Hor C₁₋₁₂-alkyl, and where R²⁹, R³⁰ and R³¹ are independently selectedfrom the group consisting of H, C₁₋₆-alkyl, F, Cl, Br, I, OH,O—C₁₋₆-alkyl, O-aryl¹ and O—CH₂-aryl¹, R³ and R⁴ are H, orunsubstituted, singly substituted or multiply substituted methyl, ethyl,n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl,isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, aryl′ or —CH₂-aryl′,where multiple substitution comprises replacement of multiple hydrogensbonded to one or more atoms by one or more substituents, and wherein atleast one of the radicals R³ and R⁴ is H, or one of the radicals R¹ andR² together with one of the radicals R³ and R⁴ form W, where W isα′-CH═CH—CH₂-β′, —CH═CH—CH₂—CH₂-β′, or α′-O—(CH₂)_(m)-β′ where m=2, 3, 4or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β in thecompound corresponding to structure (I A), (I B) or (II), the otherradical of R¹ and R² is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl,isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl,isohexyl or sec.-hexyl and the other radical of R³ and R⁴ is H, methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, or sec.-hexyl; R⁵ isunsubstituted, singly substituted, or multiply substituted methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, where multiplesubstitution comprises replacement of multiple hydrogens bonded to oneor more atoms by one or more substituents, or R⁵ is aryl′,—(CH₂)_(k)-aryl′ where k=1,2, 3 or 4, heterocyclyl, or C(═O)R¹¹; R⁶ isH, methyl, ethyl, —CN, fluorine, chlorine, bromine, iodine, —C(═O)R¹⁷ or—N═N-aryl¹; R⁷ is H, aryl¹, OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2, or R⁷is unsubstituted, singly substituted, or multiply substituted methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl, wheremultiple substitution comprises replacement of multiple hydrogens bondedto one or more atoms by one or more substituents, R⁸ is H or aryl′, orthe radicals R⁷ and R⁸ together form Y, where Y isγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ′ is joinedto the atom identified by γ in the compound corresponding to structure(II), and the end of Y identified by δ′ is joined to the atom identifiedby δ in the compound corresponding to structure (II); R⁹ isunsubstituted, singly substituted or multiply substituted methyl, ethyl,n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl,isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl or is—[(CH₂)_(r)—O]_(s)—H where r=1, 2, 3, 4, 5 or 6 and s=1, 2, 3, 4, 5 or6, where multiple substitution comprises replacement of multiplehydrogens bonded to one or more atoms by one or more substituents; R¹⁰is aryl′; R¹¹ is aryl′ or OR²⁵; R¹⁷ is OR²⁶; R¹⁸ is H or methyl; R¹⁹ isH, aryl¹, or unsubstituted, singly substituted or multiply substitutedmethyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl,tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl orsec.-hexyl, where multiple substitution comprises replacement ofmultiple hydrogens bonded to one or more atoms by one or moresubstituents; R²¹, R²², R²³ and R²⁴ are independently selected from thegroup consisting of H, fluorine, chlorine, bromine, iodine and OR²⁸; R²⁵is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl,tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl orsec.-hexyl, where R²⁵ is not H when both R¹ is aryl and R² is alkyl; R²⁶is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl,tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl orsec.-hexyl; R²⁸ is H, methyl or ethyl; Heterocyclyl is furan-2-yl,furan-3-yl, thien-2-yl, thien-3-yl, pyridin-2-yl, pyridin-3-yl orpyridin-4-yl, where furanyl, thienyl and pyridinyl are unsubstituted,singly substituted or multiply substituted, and where multiplesubstitution comprises replacement of multiple hydrogens bonded to oneor more atoms by one or more substituents; R²⁹, R³⁰ and R³¹, whenoccurring within R³, R⁴, R⁵, R⁷, R⁸, R¹⁰, R¹¹, or R¹⁹, are independentlyselected from the group consisting of H, C₁₋₆-alkyl, C₃₋₈-cycloalkyl,(C₁₋₆ alkyl)-C₃₋₈-cycloalkyl, aryl, (C₁₋₆-alkyl)-aryl, heterocyclyl,(C₁₋₆ alkyl)-heterocyclyl, F, Cl, Br, I, —CN, —NC, —OR³², —SR³³, —NO,—NO₂, NH₂, NHR³⁴, NR³⁵R³⁶, —N—OH, —N—OC₁₋₆-alkyl, —NHNH₂, —N═N-aryl,—(C═O)R³⁷, —(C═S)R³⁷, or

 where d=1, 2 or 3, and may be in any arbitrary ring position; R³² andR³³ are independently selected from the group consisting of H,—C₁₋₆-alkyl, —C₃₋₈-cycloalkyl, —(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl,—(C₁₋₆-alkyl)-aryl,  -heterocyclyl, —(C₁₋₆-alkyl)-heterocyclyl,(C═O)R³⁸, —[(CH₂)_(w)—O]_(z)—H or —[(CH₂)_(w)—O]_(z)—C₁₋₆-alkyl where w1, 2, 3 or 4 and z=1, 2, 3, 4 or 5; R³⁴ is C₁₋₆-alkyl, —CH₂-aryl or—(C═O)O-tert.-butyl; R³⁵ and R³⁶ are C₁₋₆-alkyl or together are—(CH₂)_(g)— and form a ring where g=4 or 5; R³⁷ is H, —C₁₋₆-alkyl,—C₃₋₈-cycloalkyl, —(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl,—(C₁₋₆-alkyl)-aryl, -heterocyclyl, —(C₁₋₆-alkyl)-heterocyclyl, —OR³⁹,—NH₂, —NHR³⁴, NR³⁵R³⁶; R³⁸ is H, —C₁₋₆-alkyl, —C₃₋₈-cycloalkyl,—(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl, —(C₁₋₆-alkyl)-aryl; and R³⁹ is H,—C₁₋₆-alkyl, —C₃₋₈-cycloalkyl, —(C₁₋₆-alkyl)-C₃₋₈-cycloalkyl, -aryl,—(C₁₋₆-alkyl)-aryl, -heterocyclyl or —(C₁₋₆-alkyl)-heterocyclyl.
 6. Acompound according to claim 1, wherein R¹ and R² are independentlyselected from the group consisting of H, O—R⁹, S—R¹⁰, or unsubstituted,singly substituted, or multiply substituted methyl, ethyl, n-propyl,2-propyl, n-butyl, tert.-butyl or n-hexyl, aryl′ or —CH₂-aryl′, wherearyl′ is aryl¹, aryl², or aryl³,

 where R²⁹, R³⁰ and R³¹ are independently selected from the groupconsisting of H, methyl, ethyl, 2-propyl, n-butyl, tert.-butyl, n-hexyl,F, Cl, Br, I, OH, O-methyl, and O-ethyl,  wherein exactly one of R¹ andR² is H, or wherein one of the radicals R¹ and R² is aryl′ and the otherradical of R¹ and R² is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl,tert.-butyl or n-hexyl, R³ and R⁴ are independently selected from thegroup consisting of H, methyl or aryl¹, wherein the aryl¹ substituentsR²⁹, R³⁰ and R³¹ are independent selected from the group consisting ofH, methyl and O-methyl,  wherein at least one of the radicals R³ and R⁴is H, or one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ form W, where W is α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′,α′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β in thecompound corresponding to structure (I A), (I B) or (II), and the otherradical of R¹ and R² and the other radical of R³ and R⁴ is H; R⁵ ismethyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl,tert.-butyl, —(CH₂)₄—OH, cyclopropyl that is unsubstituted or singlysubstituted by C(═O)OH, C(═O)O-methyl or C(═O)O-ethyl, cyclopentyl,cyclohexyl, aryl¹ or —(CH₂)_(k)-aryl¹ where the aryl¹ substituents R²⁹,R³⁰ and R³¹ are independently selected from the group consisting of H,—OH, —O-methyl, O—C₆H₅, CH₃, CF₃ or C(═O)OH and k=1 or 2, or R⁵ isheterocyclyl or C(═O)R¹¹; R⁶ is H, —CN, bromine, —C(═O)R¹⁷ or—N═N-phenyl; R⁷ is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl,isobutyl, sec.-butyl or tert.-butyl, or aryl¹ where R²⁹, R³⁰ and R³¹ areindependently selected from the group consisting of H, OH, orS(O)_(q)R¹⁹ where q=0 or 2, R⁸ is H, aryl¹ where the aryl¹ substituentsR²⁹, R³⁰ and R³¹ are independently selected from the group consisting ofH, methyl or chlorine, or aryl³ where R²⁹, R³⁰ and R³¹ are H, or theradicals R⁷ and R⁸ together form Y, where Y isγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ′ is joinedto the atom identified by γ in the compound corresponding to structure(II), and the end of Y identified by δ′ is joined to the atom identifiedby δ in the compound corresponding to structure (II); R⁹ is methyl,ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl,cyclopentyl, cyclohexyl, or —[(CH₂)_(r)—O]_(s)—H where r=1, 2 or 3 ands=1 or 2; R¹⁰ is aryl¹; R¹¹ is aryl¹ where R²⁹, R³⁰ and R³¹ are H orOR²⁵; R¹⁷ is OR²⁶; R¹⁹ is methyl or aryl¹, where one of the aryl¹substituents R²⁹, R³⁰ and R³¹ is H or —NO₂, and the two other aryl¹substituents of R²⁹, R³⁰ and R³¹ are H; R²¹ and R²³ are H; R²² is H,fluorine or OR²⁶; R²⁴ is H or chlorine; R²⁵ is H, methyl or ethyl, whereR²⁵ is not H when R¹ is aryl and R² is alkyl; R²⁶ is H, methyl or ethyl;R²⁸ is methyl or ethyl; and Heterocyclyl is furan-2-yl, furan-3-yl,thien-2-yl, thien-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl,where furanyl, thienyl and pyridinyl are unsubstituted, singlysubstituted, or multiply substituted by —NO₂, CH₃ or C(═O)OH, wheremultiple substitution comprises replacement of multiple hydrogens bondedto one or more atoms by one or more substituents.
 7. A compoundaccording to claim 1, wherein R¹ and R² are independently selected fromthe group consisting of H, O—CH₂—CH₂—OH, O-cyclohexyl, S-phenyl, methyl,phenyl, 3-fluorophenyl, 3-bromophenyl, 4-bromophenyl, 4-chlorophenyl,4-fluorophenyl, 3-methylphenyl, 4-hydroxyphenyl, 4-methoxyphenyl,2,4-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3,4-trimethoxyphenyl,2-naphthyl or —CH₂-phenyl, R³ and R⁴ are H, methyl or 4-methoxyphenyl,where at least one of R³ and R⁴ is H, or one of the radicals R¹ and R²together with one of the radicals R³ and R⁴ form W, where W isα′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′, or α′-O—(CH₂)_(m)-β′ where m=2, 3,4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β in thecompound corresponding to structure (I A), (I B) or (II), and the otherradical of R¹ and R² and the other radical of R³ and R⁴ are H; R⁵ isn-propyl, n-butyl, tert.-butyl, —(CH₂)₄—OH, cyclopropyl,cycloprop-2-yl-1-carboxylic acid ethyl ether, cyclohexyl,4-trifluorophenyl, 4-phenoxyphenyl, 2-hydroxy-3-methoxyphenyl,4-hydroxy-3-methoxyphenyl, 3-carboxy-2-hydroxyphenyl, —(CH₂)₂-phenyl,5-carboxyfuran-2-yl, 5-methylfuran-2-yl, 5-nitrofuran-2-yl,5-nitrothien-2-yl, pyridin-2-yl, pyridin-3-yl, C(═O)-phenyl, C(═O)OH orC(═O)Oethyl, where R⁵ is not C(═O)OH when both R¹ is aryl and R² isalkyl; R⁶ is H, —CN, bromine, —C(═O)OH, —C(═O)Oethyl or —N═N-phenyl; R⁷is H, phenyl, OH, —S-methyl, —SO₂-(4-nitrophenyl) or tert.-butyl; R⁸ is4-chlorophenyl, 4-methylphenyl or 2-naphthyl; or the radicals R⁷ and R⁸together form Y, where Y is γ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end ofY identified by γ′ is joined to the atom identified by γ in the compoundcorresponding to structure (II), and the end of Y identified by δ′ isjoined to the atom identified by δ in the compound corresponding tostructure (II); and R²¹ is fluorine, methoxy or ethoxy.
 8. A compoundaccording to claim 1, wherein the compound is selected from the groupconsisting of:3-bromo-5-(5-nitrofuran-2-yl)-7-m-tolyltetrahydropyrazolo[1,5-a]pyrimidine3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-7-naphthalin-2-yl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine2-(3-bromo-7-m-tolyltetrahydropyrazolo[1,5-a]-pyrimidin-5-yl)-cyclopropanecarboxylicacid ethyl ester2-[3-bromo-7-(4-bromophenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester2-(3-bromo-7-naphthalin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-cyclopropanecarboxylicacid ethyl ester3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-methylfuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-7-(4-methoxyphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic aciddiethyl ester;5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic aciddiethyl ester2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester;3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylicacid ethyl ester7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid diethyl ester3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester2-hydroxy-7-(4-hydroxyphenyl)-6-methyl-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-bromo-7-(4-hydroxyphenyl)-6-methyl-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta-[c]fluorene-3,5-dicarboxylicacid diethyl ester;5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3,5-dicarboxylicacid diethyl ester2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylicacid ethyl ester;2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylicacid ethyl ester7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid diethyl ester3-cyano-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylicacid-3-ethyl ester3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid ethyl ester7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3,5-dicarboxylicacid-3-ethyl ester3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-2-phenylazotetrahydropyrazolo[1,5-a]pyrimidine7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine7-(4-methoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(2,4-dimethylphenyl)-5-(2-ethoxycarbonylcyclopropyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester2-[7-(2,4-dimethylphenyl)-2-hydroxy-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester2-[2-tert.-butyl-7-(2,4-dimethylphenyl)tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester2-[3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester2-[3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester5-(2-ethoxycarbonylcyclopropyl)-7-(3-fluorophenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester2-[3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylicacid ethyl ester2-[7-(3-bromophenyl)-3-cyano-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(4-methoxyphenyl)-5-(5-nitrothiophen-2-yl)tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester5-[3-bromo-7-(4-methoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-furan-2-carboxylicacid5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-benzoyl-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester[3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone5-benzoyl-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(3,4-dimethoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(4-methoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-benzoyl-7-(4-methoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(4-methoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile5-benzoyl-7-(3-fluorophenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester[3-bromo-7-(3-fluorophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone[3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester3-bromo-7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile3-[3-cyano-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid3-(3-cyano-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoicacid;3-(3-cyano-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoicacid3-(3-cyano-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid3-[2-tert.-butyl-7-(4-chlorophenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoicacid5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carboxylicacid ethyl ester;5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta-[c]fluorene-3-carboxylicacid ethyl ester4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol;4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile5-(4-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester4-(2-tert.-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol4-(3-bromo-2-phenyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol5-(2-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(4-chlorophenyl)-5-(2-hydroxy-3-methoxyphenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile5-(4-hydroxybutyl)-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-(4-hydroxybutyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(4-chlorophenyl)-5-(4-hydroxybutyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile;5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile5-butyl-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-butyl-(4-chlorophenyl)-7-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-cyclopropyl-7-(2,4-dimethylphenyl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol2-tert.-butyl-5-cyclopropyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine5-cyclopropyl-7-(2,4-dimethylphenyl)-2-methyl-sulfanyltetrahydro-pyrazolo[1,5-a]pyrimidine-3-carbonitrile2-tert.-butyl-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine5-cyclopropyl-7-(4-methoxyphenol)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-cyclopropyl-3,5,5a,6,7,11b-hexahydro-1,4,11c-triazacyclopenta[c]phenanthrene-3-carbonitrile7-(2,4-dimethylphenyl)-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(2,4-dimethylphenyl)-3-phenylazo-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-cyclopropyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester2-(2-tert.-butyl-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-7-yloxy)-ethanol5-cyclopropyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester;5-cyclopropyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester5-cyclopropyl-3-phenylazo-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol;5-cyclopropyl-3-phenylazo-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol7-cyclohexyloxy-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carboxylicacid ethyl ester7-cyclohexyloxy-5-cyclopropyl-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-3-carbonitrile7-(4-chlorophenyl)-5-cyclohexyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carbonitrile5-cyclohexyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylicacid ethyl ester5-cyclohexyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester;5-cyclohexyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylicacid ethyl ester5-cyclohexyl-7-cyclohexyloxytetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester7-(2,4-dimethylphenyl)-3-phenylazo-5-propyltetrahydropyrazolo[1,5-a]pyrimidin-2-ol7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-propyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile5-tert.-butyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester2,5-di-tert.-butyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-5-tert.-butyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine2-[3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylicacid ethyl ester3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid4-[3-bromo-6-methyl-2-phenyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl]-phenol7-(4-hydroxyphenyl)-6-methyl-2-methylsulfanyl-5-(4-trifluoro-methylphenyl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile7-(4-hydroxyphenyl)-6-methyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile2-(4-nitrophenylsulfonyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]-pyrimidine3-(4-chlorophenyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine5-phenylsulfanyl-7-pyridin-2-yl-3-p-tolyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine7-methoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene7-ethoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene7-fluoro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene3-naphthalin-2-yl-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine7-phenyl-3-phenylazo-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester3-phenylazo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol3-bromo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-cyano-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylicacid ethyl ester3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile,and7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylicacid ethyl ester.
 9. A process for the preparation of compoundscorresponding to structure (I A) or (I B) as well as theirpharmaceutically acceptable salts

wherein R¹ and R² are independently selected from the group consistingof H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆ alkyl)-heterocyclyl, wherein exactly one of the radicals R¹ and R² is H, or wherein one ofthe radicals R¹ and R² is aryl and the other radical of R¹ and R² is Hor C₁₋₁₂-alkyl, R³ and R⁴ are selected from the group consisting of H,C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl, wherein at least one of the radicals R³ and R⁴ is H,or one of the radicals R¹ and R² together with one of the radicals R³and R⁴ form W, where W is α′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6,α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′, α′-CH═CH—CH₂—CH₂-β′,α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, or α′-O—(CH₂)_(m)-β′ wherem=2, 3, 4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A) or (I B), the end ofW identified by β′ is joined to the atom identified by β in the compoundcorresponding to structure (I A) or (I B), the other radical of R¹ andR² is H or C₁₋₁₂-alkyl, and the other radical of R³ and R⁴ is H orC₁₋₁₂-alkyl; R⁵ is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl orC(═O)R¹¹; R⁶ is H, C₁₋₈-alkyl, —CN, fluorine, chlorine, bromine, iodine,NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶ where p=0, 1 or 2, —C(═O)R¹⁷or —N═N-aryl; R⁷ is H, C₁₋₈-alkyl, aryl, —CN, fluorine, chlorine,bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁸, S(O)_(q)R¹⁹ where q=0,1 or 2, or C(═O)R²⁰, R⁹ and R¹⁰ are independently selected from thegroup consisting of H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl and —(C₁₋₆-alkyl)-aryl; R¹¹ is H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵; R¹² is C₁₋₆-alkylor —CH₂-aryl; R¹³ and R¹⁴ are identical or different C₁₋₆-alkylradicals, or together are —(CH₂)_(h)— and form a ring, where h=4 or 5;R¹⁵ and R¹⁶ are independently selected from the group consisting of H,C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl; R¹⁷ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ orOR²⁶; R¹⁸ and R¹⁹ are independently selected from the group consistingof H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl; R²⁰ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl or OR²⁷; and R²⁵, R²⁶,and R²⁷ are independently selected from the group consisting of H andC₁₋₆-alkyl, where R²⁵ is not H when both R¹ is aryl and R² is alkyl;comprising reacting a pyrazolamine corresponding to structure (IIIA) or(IIIB),

wherein R⁶ and R⁷ are as defined above in this claim, in the presence ofan acid, with an aldehyde corresponding to structure (IV)

wherein R⁵ is as defined above in this claim, and with an olefincorresponding to structure (V)

wherein R¹, R², R³ and R⁴ are as defined above in this claim, with theproviso that if one of the radicals R¹ and R² together with one of theradicals R³ and R⁴ forms W, the end of W identified by α′ is joined tothe α-carbon atom of the olefin of the general structure (V), and theend of W identified by β′ is joined to the β-carbon atom of the olefinof the general structure (V).
 10. A process according to claim 9,wherein the reaction of the heterocyclylamine corresponding to structure(III A) or (III B) with the aldehyde corresponding to structure (IV) andwith the olefin corresponding to structure (V) is carried out in aone-pot process.
 11. A process according to claim 9, wherein the acid istrifluoroacetic acid.
 12. A process according to of claim 9, wherein thereaction is carried out in an organic solvent at a temperature of 0° to100° C. and at a reaction time of 0.25 to 12 hours.
 13. A processaccording to claim 9, wherein the reaction is carried out at atemperature of 15 to 40° C.
 14. A process for the preparation ofcompounds corresponding to structure (II) or pharmaceutically acceptablesalts thereof

wherein R¹ and R² are independently selected from the group consistingof H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆ alkyl)-heterocyclyl, wherein exactly one of the radicals R¹ and R² is H, or wherein one ofthe radicals R¹ and R² is aryl and the other radical of R¹ and R² is Hor C₁₋₁₂-alkyl,  R³ and R⁴ are selected from the group consisting of H,C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl, wherein at least one of the radicals R³ and R⁴ is H,or one of the radicals R¹ and R² together with one of the radicals R³and R⁴ form W, where W is α′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6,α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′, α′-CH═CH—CH₂—CH₂-β′,α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, or α′-O—(CH₂)_(m)-β′ wherem=2, 3, 4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (II), the end of Widentified by β′ is joined to the atom identified by β in the compoundcorresponding to structure (II), the other radical of R¹ and R² is H orC₁₋₁₂-alkyl, and the other radical of R³ and R⁴ is H or C₁₋₁₂-alkyl; R⁵is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl or C(═O)R¹¹; R⁷ isH, C₁₋₈-alkyl, aryl, —CN, fluorine, chlorine, bromine, iodine, NO₂, NH₂,NHR¹², NR¹³R¹⁴, OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2, or C(═O)R²⁰, R⁸ isH, C₁₋₈-alkyl or aryl, or R⁷ and R⁸ together form Y, wherein Y isγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ′ is joinedto the atom identified by γ in the compound corresponding to structure(II), and where the end of Y identified by δ′ is joined to the atomidentified by δ in the compound corresponding to structure (II); R⁹ isC₁₋₈-alkyl, C₃₋₈-cycloalkyl or —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alklyl)-aryl; R¹⁰ is C₁₋₈-alkyl, C₃₋₈-cycloalkyl or—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alklyl)-aryl; R¹¹ is H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl or —CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵; R¹² is C₁₋₆-alkylor —CH₂-aryl; R¹³ and R¹⁴ are identical or different C₁₋₆-alkyl ortogether are —(CH₂) h- and form a ring where h=4 or 5; R¹⁸ is H,C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl; R¹⁹ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl; R²⁰ is H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl orOR²⁷; R²¹, R²², R²³ and R²⁴ are independently selected from the groupconsisting of H, fluorine, chlorine, bromine, iodine and OR²⁸; R²⁵, R²⁶,R²⁷ and R²⁸ are independently selected from the group consisting of H orC₁₋₆-alkyl, where R²⁵ is not H when both R¹ is aryl and R² is alkyl;comprising reacting a thiazolamine corresponding to structure (VI),

wherein R⁷ and R⁸ are as defined above in this claim, with the provisothat if R⁷ and R⁸ form Y, the end of Y identified by γ′ is coupled tothe atom of the thiazolamine of the general structure (VI) identified byγ and the end of Y identified by δ′ is coupled to the atom of thethiazolamine of the general structure (VI) identified by δ, in thepresence of an acid, with an aldehyde corresponding to structure (IV)

wherein R⁵ is as defined above in this claim, and with an olefincorresponding to structure (V)

wherein R¹, R², R³ and R⁴ are as defined above in this claim, with theproviso that if one of the radicals R¹ and R² together with one of theradicals R³ and R⁴ form W, the end of W identified by α′ is joined tothe α-carbon atom of the olefin corresponding to structure (V) and theend of W identified by β′ is joined to the β-carbon atom of the olefincorresponding to structure (V).
 15. A process according to claim 14,wherein the reaction of the heterocyclylamine corresponding to structure(VI) with the aldehyde corresponding to structure (IV) and with theolefin corresponding to structure (V) is carried out in a one-potprocess.
 16. A process according to claim 14, wherein the acid istrifluoroacetic acid.
 17. A process according to claim 14, wherein thereaction is carried out in an organic solvent at a temperature of 0° to100° C. and at a reaction time of 0.25 to 12 hours.
 18. A processaccording claim 14, wherein the reaction is carried out at a temperatureof 15° to 40° C.
 19. Substance library containing at least one compoundcorresponding to structure (I A), (I B) or (II)

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined in claim
 1. 20.A medicament comprising at least one compound corresponding to structure(I A), (I B) or (II)

or a salt thereof, or a solvate or hydrate thereof, or a stereoisomer,mixture of stereoisomers having an arbitrary mixture ratio, or aracemate thereof; wherein R¹ and R² are independently selected from thegroup consisting of H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆alkyl)-heterocyclyl,  wherein exactly one of the radicals R¹ and R² isH, or wherein one of the radicals R¹ and R² is aryl and the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, R³ and R⁴ are selected fromthe group consisting of H, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl, wherein at least oneof the radicals R³ and R⁴ is H, or one of the radicals R¹ and R²together with one of the radicals R³ and R⁴ form W, where W isα′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6, α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′,α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, orα′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or where W corresponds to

where the end of W identified by α′ is joined to the atom identified bya in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β in thecompound corresponding to structure (I A), (I B) or (II), the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, and the other radical of R³and R⁴ is H or C₁₋₁₂-alkyl; R⁵ is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆alkyl)-heterocyclyl or C(═O)R¹¹; R⁶ is H, C₁₋₈-alkyl, —CN, fluorine,chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶where p=0, 1 or 2, —C(═O)R¹⁷ or —N═N-aryl; R⁷ is H, C₁₋₈-alkyl, aryl,—CN, fluorine, chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴,OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2, or C(═O)R²⁰, R⁸ is H, C₁₋₈-alkyl oraryl, or R⁷ and R⁸ together form Y, wherein Y isγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ′ is joinedto the atom identified by γ in the compound corresponding to structure(II), and where the end of Y identified by δ′ is joined to the atomidentified by δ in the compound corresponding to structure (II); R⁹ andR¹⁰ are independently selected from the group consisting of H,C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and—(C₁₋₆-alkyl)-aryl; R¹¹ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵; R¹² is C₁₋₆-alkyl or —CH₂-aryl; R¹³and R¹⁴ are identical or different C₁₋₆-alkyl radicals, or together are—(CH₂)_(h)— and form a ring, where h=4 or 5; R¹⁵ and R¹⁶ areindependently selected from the group consisting of H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and —(C₁₋₆-alkyl)-aryl; R¹⁷is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl,—(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ or OR²⁶; R¹⁸ and R¹⁹ areindependently selected from the group consisting of H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl; R²⁰is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl or OR²⁷; R²¹, R²², R²³ and R²⁴ are independentlyselected from the group consisting of H, fluorine, chlorine, bromine,iodine and OR²⁸; R²⁵, R²⁶, R²⁷ and R²⁸ are independently selected fromthe group consisting of H or C₁₋₆-alkyl, where R²⁵ is not H when both R¹is aryl and R² is alkyl; and a pharmaceutically acceptable carrier. 21.A medicament according to claim 20, wherein the compound correspondingto structure (I A), (I B) or (II) is present as a physiologicallycompatible salt.
 22. A medicament according to claim 20, wherein thecompound corresponding to structure (I A), (I B) or (II) is present as apure enantiomer or a pure diastereomer.
 23. A medicament according toclaim 20, wherein the compound corresponding to structure (I A), (I B)or (II) is present as a mixture of enantiomers or a mixture ofstereoisomers.
 24. A method for treating pain comprising administering apharmaceutically effective amount of a compound corresponding tostructure (I A), (I B) or (II)

or a or salt thereof, or a solvate or hydrate thereof, or astereoisomer, mixture of stereoisomers having an arbitrary mixtureratio, or a racemate thereof; wherein R¹ and R² are independentlyselected from the group consisting of H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl,heterocyclyl or —(C₁₋₆ alkyl)-heterocyclyl,  wherein exactly one of theradicals R¹ and R² is H, or wherein one of the radicals R¹ and R² isaryl and the other radical of R¹ and R² is H or C₁₋₁₂-alkyl, R³ and R⁴are selected from the group consisting of H, C₁₋₁₂-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl,wherein at least one of the radicals R³ and R⁴ is H, or one of theradicals R¹ and R² together with one of the radicals R³ and R⁴ form W,where W is α′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6, α′-CH═CH—CH₂-β′,α′-CH₂—CH═CH-β′, α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂—β′,α′-CH₂—CH₂—CH═CH-β′, or α′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or whereW corresponds to

where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A), (I B) or (II), theend of W identified by β′ is joined to the atom identified by β in thecompound corresponding to structure (I A), (I B) or (II), the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, and the other radical of R³and R⁴ is H or C₁₋₁₂-alkyl; R⁵ is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆alkyl)-heterocyclyl or C(═O)R¹¹; R⁶ is H, C₁₋₈-alkyl, —CN, fluorine,chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶where p=0, 1 or 2, —C(═O)R¹⁷ or —N═N-aryl; R⁷ is H, C₁₋₈-alkyl, aryl,—CN, fluorine, chlorine, bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴,OR¹⁸, S(O)_(q)R¹⁹ where q=0, 1 or 2, or C(═O)R²⁰, R⁸ is H, C₁₋₈-alkyl oraryl, or R⁷ and R⁸ together form Y, wherein Y isγ′-CR²¹═CR²²—CR²³═CR²⁴-δ′, where the end of Y identified by γ is joinedto the atom identified by γ in the compound corresponding to structure(II), and where the end of Y identified by δ′ is joined to the atomidentified by δ in the compound corresponding to structure (II); R⁹ andR¹⁰ are independently selected from the group consisting of H,C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and—(C₁₋₆-alkyl)-aryl; R¹¹ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵; R¹² is C₁₋₆-alkyl or —CH₂-aryl; R¹³and R¹⁴ are identical or different C₁₋₆-alkyl radicals, or together are—(CH₂)_(h)— and form a ring, where h=4 or 5; R¹⁵ and R¹⁶ areindependently selected from the group consisting of H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl; R¹⁷is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl,—(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ or OR²⁶; R¹⁸ and R¹⁹ areindependently selected from the group consisting of H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and —(C₁₋₆-alkyl)-aryl; R²⁰is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl or OR²⁷; R²¹, R²², R²³ and R²⁴ are independentlyselected from the group consisting of H, fluorine, chlorine, bromine,iodine and OR²⁸; R²⁵, R²⁶, R²⁷ and R²⁸ are independently selected fromthe group consisting of H or C₁₋₆-alkyl, where R²⁵ is not H when both R¹is aryl and R² is alkyl.
 25. A method according to claim 24, wherein thecompound corresponding to structure (I A), (I B) or (II) is present as aphysiologically compatible salt.
 26. A method according to claim 24,wherein the compound corresponding to structure (I A), (I B) or (II) ispresent as a pure enantiomer or a pure diastereomer.
 27. A methodaccording to claim 24, wherein the compound corresponding to structure(I A), (I B) or (II) is present as a mixture of enantiomers or a mixtureof stereoisomers.
 28. A method for treatment or prophylaxis of epilepsy,schizophrenia, neurodegenerative conditions, Alzheimer's disease,Huntington's disease and Parkinson's disease, cerebral ischaemias,infarcts, psychoses due to raised amino acid levels, cerebral oedemas,insufficiency states of the central nervous system, hypoxias, anoxias,AIDS dementia, encephalomyelitis, Tourette's syndrome, perinatalasphyxia, or tinnitus comprising administering a pharmaceuticallyeffective amount of a compound corresponding to structure (I A), (I B)or (II),

or a salt thereof, or a solvate or hydrate thereof, or a stereoisomer,mixture of stereoisomers having an arbitrary mixture ratio, or aracemate thereof; wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are asdefined in claim
 20. 29. A method according to claim 28, wherein thecompound corresponding to structure (I A), (I B) or (II) is present as aphysiologically compatible salt.
 30. A method according to claim 28,wherein the compound corresponding to structure (I A), (I B) or (II) ispresent as a pure enantiomer or a pure diastereomer.
 31. A methodaccording to claim 28, wherein the compound corresponding to structure(I A), (I B) or (II) is present as a mixture of enantiomers or a mixtureof stereoisomers.
 32. A method of ligand-binding a nucleoside transportprotein, adenosine kinase, adenosine deaminase, or A₁, A₂, or A₃receptors comprising providing a compound corresponding to formula (I A)or (I B)

or a salt thereof, or a solvate or hydrate thereof, or a stereoisomer,mixture of stereoisomers having an arbitrary mixture ratio, or aracemate thereof; wherein R¹ and R are independently selected from thegroup consisting of H, O—R⁹, S—R¹⁰, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, heterocyclyl or —(C₁₋₆alkyl)-heterocyclyl,  wherein exactly one of the radicals R¹ and R² isH, or wherein one of the radicals R¹ and R² is aryl and the otherradical of R¹ and R² is H or C₁₋₁₂-alkyl, R³ and R⁴ are selected fromthe group consisting of H, C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl, wherein at least oneof the radicals R³ and R⁴ is H, or one of the radicals R¹ and R²together with one of the radicals R³ and R⁴ form W, where W isα′-(CH₂)_(n)-β′ where n=3, 4, 5 or 6, α′-CH═CH—CH₂-β′, α′-CH₂—CH═CH-β′,α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂-β′, α′-CH₂—CH₂—CH═CH-β′, orα′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or where W corresponds to

where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A) or (I B), the end ofW identified by β′ is joined to the atom identified by β in the compoundcorresponding to structure (I A) or (I B), the other radical of R¹ andR² is H or C₁₋₁₂-alkyl, and the other radical of R³ and R⁴ is H orC₁₋₁₂-alkyl; R⁵ is C₁₋₁₂-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl,aryl, —(C₁₋₆ alkyl)-aryl, heterocyclyl, —(C₁₋₆ alkyl)-heterocyclyl orC(═O)R¹¹; R⁶ is H, C₁₋₈-alkyl, —CN, fluorine, chlorine, bromine, iodine,NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁵, S(O)_(p)R¹⁶ where p=0, 1 or 2, —C(═O)R¹⁷or —N═N-aryl; R⁷ is H, C₁₋₈-alkyl, aryl, —CN, fluorine, chlorine,bromine, iodine, NO₂, NH₂, NHR¹², NR¹³R¹⁴, OR¹⁸, S(O)_(q)R¹⁹ where q=0,1 or 2, or C(═O)R²⁰, R⁹ and R¹⁰ are independently selected from thegroup consisting of H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl and —(C₁₋₆-alkyl)-aryl; R¹¹ is H, C₁₋₈-alkyl,C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or OR²⁵; R¹² is C₁₋₆-alkylor —CH₂-aryl; R¹³ and R¹⁴ are identical or different C₁₋₆-alkylradicals, or together are —(CH₂)_(h)— and form a ring, where h=4 or 5;R¹⁵ and R¹⁶ are independently selected from the group consisting of H,C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl or—(C₁₋₆-alkyl)-aryl; R¹⁷ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl, —(C₁₋₆-alkyl)-aryl, NH₂, NHR¹², NR¹³R¹⁴ orOR²⁶; R¹⁸ and R¹⁹ are independently selected from the group consistingof H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, —CH₂—C₃₋₈-cycloalkyl, aryl and—(C₁₋₆-alkyl)-aryl; R²⁰ is H, C₁₋₈-alkyl, C₃₋₈-cycloalkyl,—CH₂—C₃₋₈-cycloalkyl, aryl or —(C₁₋₆-alkyl)-aryl or OR²⁷; R²⁵, R²⁶ andR²⁷ are independently selected from the group consisting of H orC₁₋₆-alkyl, where R²⁵ is not H when both R¹ is aryl and R² is alkyl; inthe presence of a nucleoside transport protein, adenosine kinase,adenosine deaminase, or A₁, A₂, or A₃ receptors.
 33. A method accordingto claim 32, wherein the compound corresponding to structure (I A) or (IB) is present as a physiologically compatible salt.
 34. A methodaccording to claim 32, wherein the compound corresponding to structure(I A) or (I B) is present as a pure enantiomer or a pure diastereomer.35. A method according to claim 32, wherein the compound correspondingto structure (I A) or (I B) is present as a mixture of enantiomers or amixture of stereoisomers.
 36. A method for preventing or treating amedical condition or illness affected by modulating nucleoside transportproteins, adenosine kinase, adenosine deaminase, or A₁, A₂, or A₃receptors comprising administering a pharmaceutically effective amountof a compound corresponding to formula (I A) or (I B)

or an acid, base, or salt thereof, or a solvate or hydrate thereof, or astereoisomer, mixture of stereoisomers having an arbitrary mixtureratio, or a racemate thereof; wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areas defined in claim
 32. 37. A method according to claim 36, wherein thecompound corresponding to structure (I A) or (I B) is present as aphysiologically compatible salt.
 38. A method according to claim 36,wherein the compound corresponding to structure (I A) or (I B) ispresent as a pure enantiomer or a pure diastereomer.
 39. A methodaccording to claim 36, wherein the compound corresponding to structure(I A) or (I B) is present as a mixture of enantiomers or a mixture ofstereoisomers.
 40. A method for preventing or treating pain, neuropathicpain, respiratory pathway conditions, cancer, cardiac arrhythmias,ischaemias, epilepsy, Huntington's disease, malfunctions and diseases ofthe immune system, inflammatory conditions and diseases, neonatalhypoxia, neurodegenerative conditions, Parkinson's disease, kidneyfailure, schizophrenia, sleep disturbances, strokes, thromboses, urinaryincontinence, diabetes, psoriasis, septic shock, cerebral trauma,glaucoma or congestive insufficiency comprising administering apharmacuetically effective amount of a medicament according to claim 20.41. The method of claim 36, wherein R¹ and R² are independently selectedfrom the group consisting of H, O—CH₂—CH₂—OH, O-cyclohexyl, S-phenyl,methyl, phenyl, 3-fluorophenyl, 3-bromophenyl, 4-bromophenyl,4-chlorophenyl, 4-fluorophenyl, 3-methylphenyl, 4-hydroxyphenyl,4-methoxyphenyl, 2,4-dimethylphenyl, 3,4-dimethoxyphenyl,2,3,4-trimethoxyphenyl, 2-naphthyl and —CH₂-phenyl, R³ and R⁴ are H,methyl or 4-methoxyphenyl, where at least one of the radicals R³ and R⁴is H, or one of the radicals R¹ and R² together with one of the radicalsR³ and R⁴ form W,  where W is α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′, orα′-O—(CH₂)_(m)-β′ where m=2, 3, 4 or 5, or where W corresponds to

 where the end of W identified by α′ is joined to the atom identified byα in the compound corresponding to structure (I A) or (I B), the end ofW identified by β′ is joined to the atom identified by β in the compoundcorresponding to structure (I A) or (I B), and the other radical of R¹and R² and the other radical R³ and R⁴ are H; R⁵ is n-propyl, n-butyl,tert.-butyl, —(CH₂)₄—OH, cyclopropyl, cycloprop-2-yl-1-carboxylic acidethyl ether, cyclohexyl, 4-trifluorophenyl, 4-phenoxyphenyl,2-hydroxy-3-methoxyphenyl, 4-hydroxy-3-methoxyphenyl,3-carboxy-2-hydroxyphenyl, —(CH₂)₂-phenyl, 5-carboxyfuran-2-yl,5-methylfuran-2-yl, 5-nitrofuran-2-yl, 5-nitrothien-2-yl, pyridin-2-yl,pyridin-3-yl, C(═O)-phenyl, C(═O)OH or C(═O)Oethyl, where R⁵ is notC(═O)OH when both R¹ is aryl and R² is alkyl; R⁶ is H, —CN, bromine,—C(═O)OH, —C(═O)Oethyl or —N═N-phenyl; and R⁷ is H, phenyl, OH,—S-methyl, —SO₂-(4-nitrophenyl) or tert.-butyl.
 42. A pharmaceuticalcomposition comprising at least one compound corresponding to structure(I A), (I B) or (II)

or a salt thereof, or a solvate or hydrate thereof, or a stereoisomer,mixture of stereoisomers having an arbitrary mixture ratio, or aracemate thereof; wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are asdefined in claim 1; and at least one pharmaceutical auxiliary substance.